Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane
Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane
复制标题
DOI：
10.1002/ajoc.201600472
复制
发表时间：
2017-01-01
影响因子：
2.7
通讯作者：
Kondo, Yoshinori
中科院分区：
文献类型：
--
作者：
Nozawa-Kumada, Kanako;Inagi, Moeto;Kondo, Yoshinori
描述了1,3-二甲基-3,4,5,6-四氢- 2(1H)-嘧啶酮（DMPU）中末端炔与三氟甲基三烷基硅烷的化学选择性硅基化反应。该工艺即使在温和的条件下也有效，不使用氟化物或n -杂环碳（NHC），为合成炔基硅化合物提供了一种广泛适用的方法。此外，还发现该体系对末端炔的优先去质子化比醛、酮和酯的三氟甲基化进行得更快。
A chemoselective silylation of terminal alkynes with trifluoromethyltrialkylsilane in 1,3-dimethyl-3,4,5,6-tetrahydro- 2(1H)-pyrimidinone (DMPU) is described. This process is effective even under mild conditions without the use of fluorides or an N-heterocyclic carbene (NHC), providing a widely applicable method for the synthesis of alkynylsilicon compounds. Moreover, it was found that the preferential deprotonation of terminal alkynes using this system proceeded faster than the trifluoromethylation of aldehydes, ketones, and esters.