Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols

Chuchelkin, I.V.; Gavrilov, K.N.; Gavrilov, V.K.; Zheglov, S.V.; Firsin, I.D.; Perepukhov, A.M.; Maximychev, A.V.; Borisova, N.E.; Zamilatskov, I.A.; Tyurin, V.S.; Dejoie, C.; Chernyshev, V.V.; Zimarev, V.; Goulioukina, N.S.

Статья опубликована в высокорейтинговом журнале

Информация о цитировании статьи получена из Scopus, Web of Science
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 22 декабря 2021 г.

Авторы: Chuchelkin Ilya V., Gavrilov Konstantin N., Gavrilov Vladislav K., Zheglov Sergey V., Firsin Ilya D., Perepukhov Alexander M., Maximychev Alexander V., Borisova Nataliya E., Zamilatskov Ilya A., Tyurin Vladimir S., Dejoie Catherine, Chernyshev Vladimir V., Zimarev V., Goulioukina Nataliya S.
Журнал: Organometallics
Том: 40
Номер: 21
Год издания: 2021
Издательство: American Chemical Society
Местоположение издательства: United States
Первая страница: 3645
Последняя страница: 3658
DOI: 10.1021/acs.organomet.1c00491
Аннотация: A large family of P,S-bidentate diamidophosphite ligands were readily synthesized from accessible hydroxyl-thioether compounds. One type of Pd(II) cationic allylic complex with these diamidophosphites fulfilling a P-monodentate function, and three types, where the ligands act as P,S-bridging ligands (coordination polymer and head-to-head and head-to-tail dimers), were obtained. In addition, neutral Pd(II) halide complexes were generated in situ as common intermediates for both groups of cationic dimers. The structures of the ligands and complexes were elucidated by means of 2D-NMR and were confirmed by powder X-ray diffraction, as well as by DFT calculations. Asymmetric inducers of this type exhibited up to 94% ee in the Pd-mediated allylic substitution of (E)-1,3-diphenylallyl acetate with various C- and N-nucleophiles. Ee values of up to 80% were obtained in the Pd-catalyzed allylic alkylation of cinnamyl acetate with β-ketoesters. In addition, up to 61% ee was achieved in the asymmetric amination of 2-(diethoxyphosphoryl)-1-phenylallyl acetate with aniline. The effects of the diamidophosphite and thioether moieties on the catalytic activity and enantioselectivity were investigated.
Добавил в систему: Замилацков Илья Алексеевич

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Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcoholsстатья

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