Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane

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• 作者：Kanako Nozawa-Kumada ; Moeto Inagi and Prof. Dr. Yoshinori Kondo
• 刊名：Asian Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：6
• 期：1
• 页码：63-66
• 全文大小：437K
• ISSN：2193-5815

文摘

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.