N-heterocyclic carbene catalyzed intramolecular acylation of allylic electrophiles.
N-heterocyclic carbene catalyzed intramolecular acylation of allylic electrophiles.
复制标题
DOI：
10.1021/ol501046p
复制
发表时间：
2014-05
期刊：
影响因子：
5.2
通讯作者：
Minggang Zhao;Hui Yang;Miao‐Miao Li;Jie Chen;Ling Zhou
中科院分区：
文献类型：
--
作者：
Minggang Zhao;Hui Yang;Miao‐Miao Li;Jie Chen;Ling Zhou
氮杂环卡宾（NHC）催化的加成反应是近年来研究的热点，然而，NHC催化的取代反应，尤其是SN 2 '型反应仍然是一个挑战。作为有机化学中最基本的反应类型之一，NHC催化的SN 2 '反应将成为有机合成的有力工具。因此，第一个NHC催化的醛与烯丙基亲电试剂的分子内SN 2 '取代反应已经发展。通过多米诺SN 2 '反应和异构化反应，得到了多种α，β-不饱和色满酮。进行机理实验以确认该SN 2 '反应的性质。
The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the SN2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the SN2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular SN2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of α,β-unsaturated chromanones were obtained under a domino SN2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this SN2' reaction.