chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2023-18-4-355-380chemicallytech-1991Research ArticleCHEMISTRY AND TECHNOLOGY OF ORGANIC SUBSTANCESХИМИЯ И ТЕХНОЛОГИЯ ОРГАНИЧЕСКИХ ВЕЩЕСТВPalladium-catalyzed allylation of norbornadiene: Experimental and quantum chemical researchПалладий-катализируемое аллилирование норборнадиена: Экспериментальные и квантово-химические исследованияhttps://orcid.org/0000-0003-4842-3283ДураковC. А.DurakovS. A.

Дураков Сергей Алексеевич, к.х.н., доцент кафедры аналитической химии им. И.П. Алимарина, старший научный сотрудник кафедры физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 57194217518, ResearcherID AAS-6578-2020

Sergey A. Durakov, Cand. Sci. (Chem.), Associate Professor, Department of Analytical Chemistry and Senior Researcher, Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

s.a.durakov@mail.ruhttps://orcid.org/0000-0002-7942-4011ЕгиазарянК. Т.EgiazaryanK. T.

Егиазарян Карен Тигранович, аспирант кафедры физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 57222128479

Karen T. Egiazaryan, Postgraduate Student, Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

mccubas369@gmail.comhttps://orcid.org/0000-0002-0473-770XШамсиевР. С.ShamsievR. S.

Шамсиев Равшан Сабитович, д.х.н., профессор кафедры физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 6506076152, ResearcherID L-4526-2016

Ravshan S. Shamsiev, Dr. Sci. (Chem.), Professor of the Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

shamsiev.r@gmail.comhttps://orcid.org/0000-0001-6559-5648ФлидВ. Р.FlidV. R.

Виталий Рафаилович Флид, д.х.н., профессор, заведующий кафедрой физической химии им. Я.К. Сыркина

119571, Москва, пр-т Вернадского, д. 86

Scopus Author ID 6602997346, ResearcherID H-1781-2017

Vitaly R. Flid, Dr. Sci. (Chem.), Professor, Head of the Department of Physical Chemistry

86, Vernadskogo pr., Moscow, 119571

vitaly-flid@yandex.ruМИРЭА – Российский технологический университет (Институт тонких химических технологий им. М.В. Ломоносова)РоссияMIREA – Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)Russian Federation202308102023184355380Copyright © Durakov S.A., Egiazaryan K.T., Shamsiev R.S., Flid V.R., 20232023Дураков C.А., Егиазарян К.Т., Шамсиев Р.С., Флид В.Р.Durakov S.A., Egiazaryan K.T., Shamsiev R.S., Flid V.R.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/1991Objectives

Objectives. Catalytic processes involving norbornadiene (NBD) and norbornene (NBN) derivatives provide exceptional opportunities for the synthesis of a wide range of carbocyclic hydrocarbons. By significantly expanding this range, it becomes possible to obtain materials offering a wide variety of predictable properties. The aim of the present review is to summarize the latest achievements in the creation of novel processes catalyzed by palladium compounds. Considerable attention is paid to the study of the mechanisms of NBD allylation reactions by a combination of experimental and theoretical methods.

Results

Results. Various strategies of the molecular design of palladium catalysts for syntheses based on NBN and NBD are considered. The possibility of implementing various directions of NBD allylation is demonstrated. Factors influencing the direction of the reactions, by which means individual products can be selectively obtained, are discussed.

Conclusions

Conclusions. The effective development of new catalytic processes involving NBD and NBN derivatives requires the complex application of synthetic, kinetic, isotopic, and quantum chemical approaches. By combining instrumental and theoretical methods with constant feedback, it becomes possible to optimize the search for original catalytic systems, obtain information about the mechanisms of their action, and influence technological parameters in a targeted manner.

Цели

Цели. Каталитические процессы с участием норборнадиена (НБД) и производных норборненового (НБН) ряда открывают исключительные возможности для синтеза широкого круга карбоциклических углеводородов. Значительное расширение их ассортимента позволяет впоследствии получать материалы с широким спектром прогнозируемых свойств. Целью обзора является обобщение последних достижений в области создания новых процессов, катализируемых соединениями палладия. Значительное внимание уделено исследованию механизмов группы реакций аллилирования НБД совокупностью экспериментальных и теоретических методов.

Результаты

Результаты. Рассмотрены различные стратегии молекулярного дизайна палладиевых катализаторов для синтезов на основе НБН и НБД. Показана возможность реализации различных направлений аллилирования НБД. Обсуждены факторы, влияющие на направление реакций и позволяющие селективно получать индивидуальные продукты.

Выводы

Выводы. Разработка новых каталитических процессов с участием НБД и НБН-производных требует комплексного применения синтетических, кинетических, изотопных и квантово-химических подходов. Совокупность инструментальных и теоретических методов, имеющих обратные связи, позволяет оптимизировать поиск оригинальных каталитических систем, получать информацию о механизмах их действия и направленно влиять на технологические параметры.

норборненнорборнадиеналлилированиекатализкинетикаквантово-химические расчетымеханизм реакциипереходные металлыпалладийнапряженные карбоциклические соединенияnorbornenenorbornadieneallylationcatalysiskineticsquantum chemical calculationsreaction mechanismtransition metalspalladiumstrained carbocyclic compoundsРабота выполнена при финансовой поддержке гранта Российского научного фонда (проект № 23-73-00123), с использованием оборудования Центра коллективного пользования РТУ МИРЭА (соглашение № 075-15-2021-689 от 01.09.2021 г, уникальный идентификационный номер 2296.61321X0010). Квантово-химические расчеты проведены с использованием вычислительных ресурсов Межведомственного суперкомпьютерного центра Российской Академии Наук.The work was supported by the Russian Science Foundation (project No. 23-73-00123) and performed using the equipment of the Shared Science and Training Center for Collective Use of RTU MIREA (agreement No. 075-15-2021-689 dated 01.09.2021 (unique identification number 2296.61321Х0010). Quantum-chemical calculations were carried out using the computing resources of the Joint Supercomputer Center of the Russian Academy of Sciences.ReferencesButt N.A., Zhang W. Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates. Chem. Soc. Rev. 2015;44(22):7929–7967. https://doi.org/10.1039/C5CS00144GButt N.A., Zhang W. Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates. Chem. Soc. Rev. 2015;44(22):7929–7967. https://doi.org/10.1039/C5CS00144GDutta S., Bhattacharya T., Werz D.B., Maiti D. Transition-metal-catalyzed C–H allylation reactions. Chem. 2021;7(3):555–605. https://doi.org/10.1016/j.chempr.2020.10.020Dutta S., Bhattacharya T., Werz D.B., Maiti D. Transition-metal-catalyzed C–H allylation reactions. Chem. 2021;7(3):555–605. https://doi.org/10.1016/j.chempr.2020.10.020Pàmies O., Margalef J., Cañellas S., James J., Judge E., Guiry P.J., et al. Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications. Chem. Rev. 2021;121(8):4373–4505. https://doi.org/10.1021/acs.chemrev.0c00736Pàmies O., Margalef J., Cañellas S., James J., Judge E., Guiry P.J., et al. Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications. Chem. Rev. 2021;121(8):4373–4505. https://doi.org/10.1021/acs.chemrev.0c00736Geurts K., Fletcher S.P., van Zijl A.W., Minnaard A.J., Feringa B.L. Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents. Pure Appl. Chem. 2008;80(5):1025–1037. https://doi.org/10.1351/pac200880051025Geurts K., Fletcher S.P., van Zijl A.W., Minnaard A.J., Feringa B.L. Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents. Pure Appl. Chem. 2008;80(5):1025–1037. https://doi.org/10.1351/pac200880051025Cheng Q., Tu H.-F., Zheng C., Qu J.-P., Helmchen G., You S.-L. Iridium-Catalyzed Asymmetric Allylic Substitution Reactions. Chem. Rev. 2019;119(3):1855–1969. https://doi.org/10.1021/acs.chemrev.8b00506Cheng Q., Tu H.-F., Zheng C., Qu J.-P., Helmchen G., You S.-L. Iridium-Catalyzed Asymmetric Allylic Substitution Reactions. Chem. Rev. 2019;119(3):1855–1969. https://doi.org/10.1021/acs.chemrev.8b00506Kazmaier U. (Ed.). Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis. 2012th edition. Berlin Heidelberg: Springer; 2011. 628 p.Kazmaier U. (Ed.). Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis. 2012th edition. Berlin Heidelberg: Springer; 2011. 628 p.Ghorai D., Cristòfol À., Kleij A.W. Nickel‐Catalyzed Allylic Substitution Reactions: An Evolving Alternative. Eur. J. Inorg. Chem. 2022;2022(2):e202100820. https://doi.org/10.1002/ejic.202100820Ghorai D., Cristòfol À., Kleij A.W. Nickel‐Catalyzed Allylic Substitution Reactions: An Evolving Alternative. Eur. J. Inorg. Chem. 2022;2022(2):e202100820. https://doi.org/10.1002/ejic.202100820Mizutani K., Yorimitsu H., Oshima K. Cobalt-Catalyzed Allylic Substitution Reaction of Allylic Ethers with Phenyl and Trimethylsilylmethyl Grignard Reagents. Chem. Lett. 2004;33(7):832–833. https://doi.org/10.1246/cl.2004.832Mizutani K., Yorimitsu H., Oshima K. CobaltCatalyzed Allylic Substitution Reaction of Allylic Ethers with Phenyl and Trimethylsilylmethyl Grignard Reagents. Chem. Lett. 2004;33(7):832–833. https://doi.org/10.1246/cl.2004.832Mohammadkhani L., Heravi M.M. Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update. Chem. Rec. 2021;21(1):29–68. https://doi.org/10.1002/tcr.202000086Mohammadkhani L., Heravi M.M. Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update. Chem. Rec. 2021;21(1):29–68. https://doi.org/10.1002/tcr.202000086Li C., Liu L., Fu X., Huang J. Norbornene in Organic Synthesis. Synthesis. 2018;50(15):2799–2823. https://doi.org/10.1055/s-0037-1610143Li C., Liu L., Fu X., Huang J. Norbornene in Organic Synthesis. Synthesis. 2018;50(15):2799–2823. https://doi.org/10.1055/s-0037-1610143Flid V.R., Gringolts M.L., Shamsiev R.S., Finkelshtein E.S. Norbornene, norbornadiene and their derivatives: promising semi-products for organic synthesis and production of polymeric materials. Russ. Chem. Rev. 2018;87(12):1169–1205. https://doi.org/10.1070/RCR4834Flid V.R., Gringolts M.L., Shamsiev R.S., Finkelshtein E.S. Norbornene, norbornadiene and their derivatives: promising semi-products for organic synthesis and production of polymeric materials. Russ. Chem. Rev. 2018;87(12):1169–1205. https://doi.org/10.1070/RCR4834Durakov S.A., Kolobov A.A., Flid V.R. Features of heterogeneous catalytic transformations of strained carbocyclic compounds of the norbornene series. Fine Chem. Technol. 2022;17(4):275–297. https://doi.org/10.32362/2410-6593-2022-17-4-275-297Durakov S.A., Kolobov A.A., Flid V.R. Features of heterogeneous catalytic transformations of strained carbocyclic compounds of the norbornene series. Fine Chem. Technol. 2022;17(4):275–297. https://doi.org/10.32362/2410-6593-2022-17-4-275-297Catellani M., Chiusoli G.P., Dradi E., Salerno G. Nickel-catalyzed allylation of norbornene. J. Organometallic Chem. 1979;177(2):C29–C31. https://doi.org/10.1016/S0022-328X(00)94094-4Catellani M., Chiusoli G.P., Dradi E., Salerno G. Nickel-catalyzed allylation of norbornene. J. Organometallic Chem. 1979;177(2):C29–C31. https://doi.org/10.1016/S0022-328X(00)94094-4Dzhemilev U.M., Khusnutdinov R.I., Galeev D.K., Nefedov O.M., Tolstikov G.A. Nickel complex-catalyzed codimerization of allyl esters with compounds in the norbornene series. Russ. Chem. Bull. 1987;36(1):122–131. https://doi.org/10.1007/BF00953861Dzhemilev U.M., Khusnutdinov R.I., Galeev D.K., Nefedov O.M., Tolstikov G.A. Nickel complex-catalyzed codimerization of allyl esters with compounds in the norbornene series. Russ. Chem. Bull. 1987;36(1):122–131. https://doi.org/10.1007/BF00953861Leont’eva S.V., Manulik O.S., Evstigneeva E.M., Bobkova E.N., Flid V.R. Unconventional catalytic allylation of 5-norbornene-2,3-dicarboxylic anhydrides: 7-oxa and 7-aza analogues. Kinet. Catal. 2006;47(3):384–388. https://doi.org/10.1134/S0023158406030098Leont’eva S.V., Manulik O.S., Evstigneeva E.M., Bobkova E.N., Flid V.R. Unconventional catalytic allylation of 5-norbornene-2,3-dicarboxylic anhydrides: 7-oxa and 7-aza analogues. Kinet. Catal. 2006;47(3):384–388. https://doi.org/10.1134/S0023158406030098Dzhemilev U.M., Khusnutdinov R.I., Galeev D.K., Tolstikov G.A. Cooligomerization of allyl acetate with norbornadiene and its derivatives catalyzed by nickel complexes. Russ. Chem. Bull. 1987;36(1):137–142. https://doi.org/10.1007/BF00953863Dzhemilev U.M., Khusnutdinov R.I., Galeev D.K., Tolstikov G.A. Cooligomerization of allyl acetate with norbornadiene and its derivatives catalyzed by nickel complexes. Russ. Chem. Bull. 1987;36(1):137–142. https://doi.org/10.1007/BF00953863Флид В.Р. Аллилирование ноборнадиена-2,5 гомолигандными η3 -аллильными комплексами переходных металлов. Металлорганическая химия. 1991;4(4):864–871. [Flid V.R. Allylation of nobornadiene-2,5 with homoligand η3 -allyl complexes of transition metals. Metallorganicheskaya Khimiya. 1991;4(4):864–871 (in Russ.).]Флид В.Р. Аллилирование ноборнадиена-2,5 гомолигандными η3 -аллильными комплексами переходных металлов. Металлорганическая химия. 1991;4(4):864–871. [Flid V.R. Allylation of nobornadiene-2,5 with homoligand η3 -allyl complexes of transition metals. Metallorganicheskaya Khimiya. 1991;4(4):864–871 (in Russ.).]Tsukada N., Sato T., Inoue Y. Palladium-catalyzed [2+2] cycloaddition of allylic acetates and norbornene. Tetrahedron Lett. 2000;41(21):4181–4184. https://doi.org/10.1016/S0040-4039(00)00600-6Tsukada N., Sato T., Inoue Y. Palladium-catalyzed [2+2] cycloaddition of allylic acetates and norbornene. Tetrahedron Lett. 2000;41(21):4181–4184. https://doi.org/10.1016/S0040-4039(00)00600-6Evstigneeva E.M., Manulik O.S., Flid V.R. Unconventional Allylation of Norbornadiene Catalyzed by Palladium Complexes. Kinet. Catal. 2004;45(2):172–175. https://doi.org/10.1023/B:KICA.0000023787.79493.e7Evstigneeva E.M., Manulik O.S., Flid V.R. Unconventional Allylation of Norbornadiene Catalyzed by Palladium Complexes. Kinet. Catal. 2004;45(2):172–175. https://doi.org/10.1023/B:KICA.0000023787.79493.e7Evstigneeva E.M., Manulik O.S., Flid V.R., Stolyarov I.P., Kozitsyna N.Yu., Vargaftik M.N., et al. Unusual selective allylation of norbornadiene in the presence of palladium nanoclusters. Russ. Chem. Bull. 2004;53(6):1345–1348. https://doi.org/10.1023/B:RUCB.0000042298.81687.ddEvstigneeva E.M., Manulik O.S., Flid V.R., Stolyarov I.P., Kozitsyna N.Yu., Vargaftik M.N., et al. Unusual selective allylation of norbornadiene in the presence of palladium nanoclusters. Russ. Chem. Bull. 2004;53(6):1345–1348. https://doi.org/10.1023/B:RUCB.0000042298.81687.ddStolyarov I.P., Gekhman A.E., Moiseev I.I., Kolesnikov A.Yu., Evstigneeva E.M., Flid V.R. Catalytic hydroallylation of norbornadiene with allyl formate. Russ. Chem. Bull. 2007;56(2):320–324. https://doi.org/10.1007/s11172-007-0052-xStolyarov I.P., Gekhman A.E., Moiseev I.I., Kolesnikov A.Yu., Evstigneeva E.M., Flid V.R. Catalytic hydroallylation of norbornadiene with allyl formate. Russ. Chem. Bull. 2007;56(2):320–324. https://doi.org/10.1007/s11172-007-0052-xEvstigneeva E.M., Flid V.R. Nonconventional allylation of norbornene and norbornadiene derivatives: stoichiometry and catalysis. Russ. Chem. Bull. 2008;57(4):837–844. https://doi.org/10.1007/s11172-008-0121-9Evstigneeva E.M., Flid V.R. Nonconventional allylation of norbornene and norbornadiene derivatives: stoichiometry and catalysis. Russ. Chem. Bull. 2008;57(4):837–844. https://doi.org/10.1007/s11172-008-0121-9Kostyukovich A.Yu., Burykina J.V., Eremin D.B., Ananikov V.P. Detection and Structural Investigation of Elusive Palladium Hydride Intermediates Formed from Simple Metal Salts. Inorg. Chem. 2021;60(10):7128–7142. https://doi.org/10.1021/acs.inorgchem.1c00173Kostyukovich A.Yu., Burykina J.V., Eremin D.B., Ananikov V.P. Detection and Structural Investigation of Elusive Palladium Hydride Intermediates Formed from Simple Metal Salts. Inorg. Chem. 2021;60(10):7128–7142. https://doi.org/10.1021/acs.inorgchem.1c00173Ragoussis V., Giannikopoulos A. Palladium catalyzed reductive decarboxylation of allyl α-alkenyl-βketoesters. A new synthesis of (E)-3-alkenones. Tetrahedron Lett. 2006;47(5):683–687. https://doi.org/10.1016/j.tetlet.2005.11.122Ragoussis V., Giannikopoulos A. Palladium catalyzed reductive decarboxylation of allyl α-alkenyl-βketoesters. A new synthesis of (E)-3-alkenones. Tetrahedron Lett. 2006;47(5):683–687. https://doi.org/10.1016/j.tetlet.2005.11.122Flid V.R., Durakov S.A., Morozova T.A. A possible way to control the course of hydride transfer in allylation of norbornadiene in the presence of palladium phosphine catalysts. Russ. Chem. Bull. 2016;65(11):2639–2643. https://doi.org/10.1007/s11172-016-1629-zFlid V.R., Durakov S.A., Morozova T.A. A possible way to control the course of hydride transfer in allylation of norbornadiene in the presence of palladium phosphine catalysts. Russ. Chem. Bull. 2016;65(11):2639–2643. https://doi.org/10.1007/s11172-016-1629-zAmatore C., Jutand A. Anionic Pd(0) and Pd(II) Intermediates in Palladium-Catalyzed Heck and Cross-Coupling Reactions. Acc. Chem. Res. 2000;33(5):314–321. https://doi.org/10.1021/ar980063aAmatore C., Jutand A. Anionic Pd(0) and Pd(II) Intermediates in Palladium-Catalyzed Heck and CrossCoupling Reactions. Acc. Chem. Res. 2000;33(5):314–321. https://doi.org/10.1021/ar980063aAmatore C., Jutand A., Amine M’Barki M. Evidence of the formation of zerovalent palladium from Pd(OAc)2 and triphenylphosphine. Organometallics. 1992;11(9):3009–3013.Amatore C., Jutand A., Amine M’Barki M. Evidence of the formation of zerovalent palladium from Pd(OAc)2 and triphenylphosphine. Organometallics. 1992;11(9):3009–3013.Amatore C., Carre E., Jutand A., M’Barki M.A. Rates and Mechanism of the Formation of Zerovalent Palladium Complexes from Mixtures of Pd(OAc)2 and Tertiary Phosphines and Their Reactivity in Oxidative Additions. Organometallics. 1995;14(4):1818–1826. https://doi.org/10.1021/om00004a039Amatore C., Carre E., Jutand A., M’Barki M.A. Rates and Mechanism of the Formation of Zerovalent Palladium Complexes from Mixtures of Pd(OAc)2 and Tertiary Phosphines and Their Reactivity in Oxidative Additions. Organometallics. 1995;14(4):1818–1826. https://doi.org/10.1021/om00004a039Negishi E., Takahashi T., Akiyoshi K. ‘Bis(triphenylphosphine)palladium:’ its generation, characterization, and reactions. J. Chem. Soc., Chem. Commun. 1986;0(17):1338–1339. https://doi.org/10.1039/C39860001338Negishi E., Takahashi T., Akiyoshi K. ‘Bis(triphenylphosphine)palladium:’ its generation, characterization, and reactions. J. Chem. Soc., Chem. Commun. 1986;0(17):1338–1339. https://doi.org/10.1039/C39860001338Durakov S.A., Melnikov P.V., Martsinkevich E.M., Smirnova A.A., Shamsiev R.S., Flid V.R. Solvent effect in palladium-catalyzed allylation of norbornadiene. Russ. Chem. Bull. 2021;70(1):113–121. https://doi.org/10.1007/s11172-021-3064-zDurakov S.A., Melnikov P.V., Martsinkevich E.M., Smirnova A.A., Shamsiev R.S., Flid V.R. Solvent effect in palladium-catalyzed allylation of norbornadiene. Russ. Chem. Bull. 2021;70(1):113–121. https://doi.org/10.1007/s11172-021-3064-zAgenet N., Amatore C., Gamez S., Gerardin H., Jutand A., Meyer G., et al. Effect of the leaving group and the allylic structure on the kinetics and thermodynamics of the reaction of allylic carboxylates with palladium(0) complexes. Arkivoc. 2005;2002(5):92–101. https://doi.org/10.3998/ark.5550190.0003.511Agenet N., Amatore C., Gamez S., Gerardin H., Jutand A., Meyer G., et al. Effect of the leaving group and the allylic structure on the kinetics and thermodynamics of the reaction of allylic carboxylates with palladium(0) complexes. Arkivoc. 2005;2002(5):92–101. https://doi.org/10.3998/ark.5550190.0003.511Yamamoto T., Saito O., Yamamoto A. Oxidative addition of allyl acetate to palladium(0) complexes. J. Am. Chem. Soc. 1981;103(18):5600–5602. https://doi.org/10.1021/ja00408a068Yamamoto T., Saito O., Yamamoto A. Oxidative addition of allyl acetate to palladium(0) complexes. J. Am. Chem. Soc. 1981;103(18):5600–5602. https://doi.org/10.1021/ja00408a068Cristol S.J., Morrill T.C., Sanchez R.A. Bridged Polycyclic Compounds. XLI. The Uncatalyzed Addition of Acetic Acid to Norbornadiene. J. Org. Chem. 1966;31(9):2733–2737. https://doi.org/10.1021/jo01347a003Cristol S.J., Morrill T.C., Sanchez R.A. Bridged Polycyclic Compounds. XLI. The Uncatalyzed Addition of Acetic Acid to Norbornadiene. J. Org. Chem. 1966;31(9):2733–2737. https://doi.org/10.1021/jo01347a003Durakov S.A., Shamsiev R.S., Flid V.R. The influence of the phosphine ligand nature on palladium catalysts in the norbornadiene allylation with allyl formate. Russ. Chem. Bull. 2021;70(7):1290–1296. https://doi.org/10.1007/s11172-021-3213-4Durakov S.A., Shamsiev R.S., Flid V.R. The influence of the phosphine ligand nature on palladium catalysts in the norbornadiene allylation with allyl formate. Russ. Chem. Bull. 2021;70(7):1290–1296. https://doi.org/10.1007/s11172-021-3213-4Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Hydride transfer mechanism in the catalytic allylation of norbornadiene with allyl formate. Russ. Chem. Bull. 2018;67(12):2234–2240. https://doi.org/10.1007/s11172-018-2361-7Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Hydride transfer mechanism in the catalytic allylation of norbornadiene with allyl formate. Russ. Chem. Bull. 2018;67(12):2234–2240. https://doi.org/10.1007/s11172-018-2361-7Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Isotope Effect in Catalytic Hydroallylation of Norbornadiene by Allyl Formate. Kinet. Catal. 2019;60(3):245–249. https://doi.org/10.1134/S0023158419030042Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E. Isotope Effect in Catalytic Hydroallylation of Norbornadiene by Allyl Formate. Kinet. Catal. 2019;60(3):245–249. https://doi.org/10.1134/S0023158419030042Shamsiev R.S., Flid V.R. Interaction of norbornadiene with allyl acetate in the presence of Ni0 complexes: a DFT modeling. Russ. Chem. Bull. 2020;69(4):653–659. https://doi.org/10.1007/s11172-020-2813-8Shamsiev R.S., Flid V.R. Interaction of norbornadiene with allyl acetate in the presence of Ni0 complexes: a DFT modeling. Russ. Chem. Bull. 2020;69(4):653–659. https://doi.org/10.1007/s11172-020-2813-8Flid V.R., Durakov S.A. New heterogenized catalytic systems in norbornadiene allylation. Russ. Chem. Bull. 2018;67(3):469–472. https://doi.org/10.1007/s11172-018-2094-7Flid V.R., Durakov S.A. New heterogenized catalytic systems in norbornadiene allylation. Russ. Chem. Bull. 2018;67(3):469–472. https://doi.org/10.1007/s11172-018-2094-7Laikov D.N. Fast evaluation of density functional exchange-correlation terms using the expansion of the electron density in auxiliary basis sets. Chem. Phys. Lett. 1997;281(1):151–156. https://doi.org/10.1016/S0009-2614(97)01206-2Laikov D.N. Fast evaluation of density functional exchange-correlation terms using the expansion of the electron density in auxiliary basis sets. Chem. Phys. Lett. 1997;281(1):151–156. https://doi.org/10.1016/S0009-2614(97)01206-2Laikov D.N., Ustynyuk Yu.A. PRIRODA-04: a quantum-chemical program suite. New possibilities in the study of molecular systems with the application of parallel computing. Russ. Chem. Bull. 2005;54(3):820–826. https://doi.org/10.1007/s11172-005-0329-xLaikov D.N., Ustynyuk Yu.A. PRIRODA-04: a quantum-chemical program suite. New possibilities in the study of molecular systems with the application of parallel computing. Russ. Chem. Bull. 2005;54(3):820–826. https://doi.org/10.1007/s11172-005-0329-xRiley K.E., Hobza P. Noncovalent interactions in biochemistry. WIREs Computational Molecular Science. 2011;1(1):3–17. https://doi.org/10.1002/wcms.8Riley K.E., Hobza P. Noncovalent interactions in biochemistry. WIREs Computational Molecular Science. 2011;1(1):3–17. https://doi.org/10.1002/wcms.8Neese F. Software update: the ORCA program system, version 4.0. WIREs Computational Molecular Science. 2018;8(1):e1327. https://doi.org/10.1002/wcms.1327Neese F. Software update: the ORCA program system, version 4.0. WIREs Computational Molecular Science. 2018;8(1):e1327. https://doi.org/10.1002/wcms.1327Perdew J.P., Burke K., Ernzerhof M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996;77(18):3865–3868. https://doi.org/10.1103/PhysRevLett.77.3865Perdew J.P., Burke K., Ernzerhof M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996;77(18):3865–3868. https://doi.org/10.1103/PhysRevLett.77.3865Laikov D.N. A new class of atomic basis functions for accurate electronic structure calculations of molecules. Chem. Phys. Lett. 2005;416(1):116–120. https://doi.org/10.1016/j.cplett.2005.09.046Laikov D.N. A new class of atomic basis functions for accurate electronic structure calculations of molecules. Chem. Phys. Lett. 2005;416(1):116–120. https://doi.org/10.1016/j.cplett.2005.09.046Najibi A., Goerigk L. The Nonlocal Kernel in van der Waals Density Functionals as an Additive Correction: An Extensive Analysis with Special Emphasis on the B97M-V and ωB97M-V Approaches. J. Chem. Theory Comput. 2018;14(11):5725–5738. https://doi.org/10.1021/acs.jctc.8b00842Najibi A., Goerigk L. The Nonlocal Kernel in van der Waals Density Functionals as an Additive Correction: An Extensive Analysis with Special Emphasis on the B97M-V and ωB97M-V Approaches. J. Chem. Theory Comput. 2018;14(11):5725–5738. https://doi.org/10.1021/acs.jctc.8b00842Pantazis D.A., Chen X.-Y., Landis C.R., Neese F. All-Electron Scalar Relativistic Basis Sets for Third-Row Transition Metal Atoms. J. Chem. Theory Comput. 2008;4(6):908–919. https://doi.org/10.1021/ct800047tPantazis D.A., Chen X.-Y., Landis C.R., Neese F. All-Electron Scalar Relativistic Basis Sets for Third-Row Transition Metal Atoms. J. Chem. Theory Comput. 2008;4(6):908–919. https://doi.org/10.1021/ct800047tRolfes J.D., Neese F., Pantazis D.A. All-electron scalar relativistic basis sets for the elements Rb–Xe. J. Computational Chem. 2020;41(20):1842–1849. https://doi.org/10.1002/jcc.26355Rolfes J.D., Neese F., Pantazis D.A. All-electron scalar relativistic basis sets for the elements Rb–Xe. J. Computational Chem. 2020;41(20):1842–1849. https://doi.org/10.1002/jcc.26355Marenich A.V., Cramer C.J., Truhlar D.G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions. J. Phys. Chem. B. 2009;113(18):6378–6396. https://doi.org/10.1021/jp810292nMarenich A.V., Cramer C.J., Truhlar D.G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions. J. Phys. Chem. B. 2009;113(18):6378–6396. https://doi.org/10.1021/jp810292nEgiazaryan K.Т., Shamsiev R.S., Flid V.R. Quantum chemical investigation of the oxidative addition reaction of allyl carboxylates to Ni(0) and Pd(0) complexes. Fine Chem. Tech. 2019;14(6):56–65. https://doi.org/10.32362/2410-6593-2019-14-6-56-65Egiazaryan K.Т., Shamsiev R.S., Flid V.R. Quantum chemical investigation of the oxidative addition reaction of allyl carboxylates to Ni(0) and Pd(0) complexes. Fine Chem. Tech. 2019;14(6):56–65. https://doi.org/10.32362/2410-6593-2019-14-6-56-65Shamsiev R.S., Egiazaryan K.T., Flid V.R. Modeling of the mechanism of reductive allylation of norbornadiene in the presence of Pd0 complexes. Russ. Chem. Bull. 2021;70(2):316–322. https://doi.org/10.1007/s11172-021-3087-5Shamsiev R.S., Egiazaryan K.T., Flid V.R. Modeling of the mechanism of reductive allylation of norbornadiene in the presence of Pd0 complexes. Russ. Chem. Bull. 2021;70(2):316–322. https://doi.org/10.1007/s11172-021-3087-5Simmons E.M., Hartwig J.F. On the interpretation of deuterium kinetic isotope effects in C–H bond functionalizations by transition-metal complexes. Angew. Chem. Int. Ed. 2012;51(13):3066–3072. https://doi.org/10.1002/anie.201107334Simmons E.M., Hartwig J.F. On the interpretation of deuterium kinetic isotope effects in C–H bond functionalizations by transition-metal complexes. Angew. Chem. Int. Ed. 2012;51(13):3066–3072. https://doi.org/10.1002/anie.201107334Shamsiev R.S., Egiazaryan K.T., Flid V.R. Allylation of norbornadiene in the presence of Pd0 phosphine complexes: a DFT modeling. Russ. Chem. Bull. 2022;71(5):905–914. https://doi.org/10.1007/s11172-022-3489-zShamsiev R.S., Egiazaryan K.T., Flid V.R. Allylation of norbornadiene in the presence of Pd0 phosphine complexes: a DFT modeling. Russ. Chem. Bull. 2022;71(5):905–914. https://doi.org/10.1007/s11172-022-3489-zEgiazaryan K.T., Shamsiev R.S., Flid V.R. Enantioselectivity of norbornadiene allylation in the presence of Pd phosphine complexes: a quantum chemical prediction. Russ. Chem. Bull. 2023;72(4):838–846. https://doi.org/10.1007/s11172-023-3847-2Egiazaryan K.T., Shamsiev R.S., Flid V.R. Enantioselectivity of norbornadiene allylation in the presence of Pd phosphine complexes: a quantum chemical prediction. Russ. Chem. Bull. 2023;72(4):838–846. https://doi.org/10.1007/s11172-023-3847-2

The authors declare that there are no conflicts of interest present.