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 OpenAlex

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W4388865375

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