催化作用
三氟甲基
镍
电泳剂
化学
醛
烷基化
基质(水族馆)
配体(生物化学)
硅烷化
反应性(心理学)
组合化学
偶联反应
有机化学
烷基
受体
病理
替代医学
地质学
海洋学
医学
生物化学
作者
Jichao Xiao,John Montgomery
标识
DOI:10.1021/acscatal.1c05801
摘要
A simple procedure is reported for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes. The process involves the catalytic reductive union of trifluoromethyl alkenes with aldehydes using a nickel complex of a 6,6'-disubstituted bipyridine ligand with zinc metal as the terminal reductant. The protocol is distinguished by its broad substrate scope, mild conditions, and simple catalytic setup. Reaction outcomes are consistent with the intermediacy of an α-silyloxy(alkyl)nickel intermediate generated by a low-valent nickel catalyst, silyl electrophile, and the aldehyde substrate. Mechanistic findings with cyclopropanecarboxaldehyde provide insights into nature of the reactive intermediates and illustrate fundamental reactivity differences that are governed by subtle changes in ligand and substrate structure.
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