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

Yan Cai; Haihong Ge; Weize Sun; Zhiwei Miao

doi:10.1055/s-0034-1380384

Synthesis, Table of Contents

Synthesis 2015; 47(11): 1669-1677
DOI: 10.1055/s-0034-1380384

paper

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

Yan Cai

^aState 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

^aState 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

^aState 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*

^aState Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China Email: miaozhiwei@nankai.edu.cn

^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. of China

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Abstract

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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.

Key words

α-diazophosphonate - C–H functionalization - S–H insertion - N,S-acetal - combined reaction

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Supplementary Material

Supporting Information