Synthesis 2015; 47(11): 1669-1677
DOI: 10.1055/s-0034-1380384
paper
© Georg Thieme Verlag Stuttgart · New York

Trifluoroborane-Catalyzed C–H Functionalization/S–H Insertion Reaction: Construction of N,S-Acetal Quaternary Centers

Yan Cai
a  State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Haihong Ge
a  State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Weize Sun
a  State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
,
Zhiwei Miao*
a  State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: miaozhiwei@nankai.edu.cn
b  Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 31 October 2014

Accepted after revision: 19 February 2015

Publication Date:
25 March 2015 (online)


Abstract

The trifluoroborane-catalyzed C–H functionalization/S–H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.

Supporting Information

 
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