卡宾
化学
催化作用
芳基
酮
基质(水族馆)
组合化学
对映选择合成
有机化学
烷基
功能群
海洋学
地质学
聚合物
作者
Yuan Cai,Lin‐Xin Ruan,Abdul Rahman,Shi‐Liang Shi
标识
DOI:10.1002/anie.202015021
摘要
Abstract A general, efficient, highly enantio‐ and chemoselective N‐heterocyclic carbene (NHC)/Ni‐catalyzed addition of readily available and stable arylboronic esters to ketones is reported. This protocol provides unexpectedly fast access (usually 10 min) to various chiral tertiary alcohols with exceptionally broad substrate scope and excellent functional group tolerance (76 examples, up to 98 % ee ). This process is orthogonal to other known Ni‐mediated Suzuki–Miyaura couplings, as it tolerates aryl chlorides, fluorides, ethers, esters, amides, nitriles, and alkyl chlorides. The reaction is applied to late‐stage modifications of various densely functionalized medicinally relevant molecules. Preliminary mechanistic studies suggest that a rare enantioselective η 2 ‐coordinating activation of ketone carbonyls is involved. This cross‐coupling‐like mechanism is expected to enable other challenging transformations of ketones.
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