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Organozinc‐Mediated Direct C−C Bond Formation via C−N Bond Cleavage of Ammonium Salts
Author(s) -
Wang DongYu,
Morimoto Koki,
Yang ZeKun,
Wang Chao,
Uchiyama Masanobu
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701132
Subject(s) - bond cleavage , cleavage (geology) , chemistry , catalysis , ammonium , coupling reaction , electron transfer , medicinal chemistry , combinatorial chemistry , photochemistry , organic chemistry , materials science , fracture (geology) , composite material
We report a direct cross‐coupling reaction between diarylzinc (Ar 2 Zn) and aryltrimethylammonium salts (ArNMe 3 + ⋅ − OTf) in the presence of LiCl, via C−N bond cleavage. The reaction takes place smoothly upon heating in THF without any external catalyst, enabling an efficient and chemoselective formation of biaryl products. Mechanistic studies indicate that the reaction proceeds through a single electron transfer route.