Sciact
  • EN
  • RU

Mechanistic insight into Pd‐catalyzed asymmetric alkylation of indoles with diazoesters employing bipyridine‐N,N’‐dioxides as chiral controllers Научная публикация

Журнал Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150
Вых. Данные Год: 2024, Том: 366, Номер: 1, Страницы: 121-133 Страниц : 13 DOI: 10.1002/adsc.202300845
Авторы Fukazawa Yasuaki 1 , Vaganov Vladimir 2 , Burykina Julia 3 , Fakhrutdinov Artem 3 , Safiullin Ruslan 2 , Plasser Felix 1 , Rubtsov Aleksandr 2 , Ananikov Valentine 3 , Malkov Andrei V. 4
Организации
1 Loughborough University School of Science, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND
2 Perm State University, RUSSIAN FEDERATION
3 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky prospect 47 Moscow 119991 Russia
4 Loughborough University, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND

Реферат: Metal-catalyzed asymmetric alkylation of indoles with α-diazoesters is well-known, however, the underlying mechanisms of this reaction, particularly the origin of stereoselectivity, remain uncertain. For the Pd catalysis, we address this cutting-edge challenge from two complementary viewpoints – i) the molecular level regarding a single catalytically active Pd center; and ii) nano-level Pd species investigating the factors favoring the appearance of the preferred catalytic centers. The formation of the active catalytic species was monitored by structural methods (NMR and ESI-MS), and metal particles were characterized with electron microscopy (SEM, EDX). On the molecular level, chiral bipyridine-N,N’-dioxides proved to be competent chiral controllers. The kinetic and DFT computational data revealed a crucial role of water in the rate and selectivity determining steps and showed that the enantioselectivity of the process is controlled by the protodepalladation step. On the nano-scale, the important effect of catalyst precursor on the overall reaction performance was shown.
Библиографическая ссылка: Fukazawa Y. , Vaganov V. , Burykina J. , Fakhrutdinov A. , Safiullin R. , Plasser F. , Rubtsov A. , Ananikov V. , Malkov A.V.
Mechanistic insight into Pd‐catalyzed asymmetric alkylation of indoles with diazoesters employing bipyridine‐N,N’‐dioxides as chiral controllers
Advanced Synthesis & Catalysis. 2024. V.366. N1. P.121-133. DOI: 10.1002/adsc.202300845 WOS OpenAlex
Идентификаторы БД:
Web of science: WOS:001114576900001
OpenAlex: W4388865375
Цитирование в БД:
БД Цитирований
OpenAlex 3
Web of science 3
Альметрики: