N-Heterocyclic carbene-catalyzed sulfa-Michael addition of enals

N-Heterocyclic carbene-catalyzed sulfa-Michael addition of enals
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N-杂环卡宾催化烯醛的磺胺-迈克尔加成

DOI:
10.1039/c7cc07269d
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发表时间:
2017
影响因子:
4.9
通讯作者:
He Lin
He Lin
中科院分区:
化学2区
文献类型:
--
作者:
Cong Zi Song;Li Yang Guo;Du Guang Fen;Gu Cheng Zhi;Dai Bin;He Lin

文献摘要

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研究了一种高效的N-杂环卡宾(NHC)催化烯醛与硫醇的磺基迈克尔加成反应(SMA)。在10mol%稳定的游离卡宾IPr催化下,以20mol%六氟异丙醇(HFIP)为添加剂,烯醛与各种硫醇反应,得到SMA加合物,产率为54-98%。在这个过程中,自由卡宾优先与硫醇通过氢键相互作用,没有观察到NHC催化的扩展Umpolung转换。
An efficient N-heterocyclic carbene (NHC) catalyzed sulfa-Michael addition (SMA) between enals and thiols has been developed. Under the catalysis of 10 mol% stable free carbene IPr and with 20 mol% hexafluoroisopropanol (HFIP) as an additive, enals react with a variety of thiols to afford the SMA adducts in 54–98% yields. In this process, the free carbene preferentially interacts with thiols through hydrogen-bonding and no NHC-catalyzed extended Umpolung transformations were observed.