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Copper‐Catalyzed Sulfenylation of Boronic Acids with Sulfonyl Hydrazides
Author(s) -
Wang TingTing,
Yang FuLai,
Tian ShiKai
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400995
Subject(s) - chemistry , sulfonyl , catalysis , acetonitrile , organic chemistry , boron , sulfur , copper , tetrafluoroborate , carbon fibers , combinatorial chemistry , polymer chemistry , alkyl , ionic liquid , materials science , composite number , composite material
An unprecedented sulfenylation reaction of carbon‐boron bonds has been developed using sulfonyl hydrazides as sulfenyl sources. A range of sulfonyl hydrazides underwent tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH 3 CN) 4 BF 4 ]/2,2′‐bipyridine‐catalyzed sulfenylation with boronic acids under air to give structurally diverse thioethers in moderate to good yields. Preliminary mechanistic studies show that sulfonyl hydrazides are subjected to decomposition into thiosulfonates and disulfides followed by formation of carbon‐sulfur bonds with boronic acids.