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Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds

Jiajia Chen, Wei Guo, Zhenrong Wang, Lin Hu, Fan Chen* and Yuanzhi Xia*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email: fanchenwzu.edu.cn, xyzwzu.edu.cn

J. Chen, W. Guo, Z. Wang, L. Hu, F. Chen, Y. Xia, J. Org. Chem., 2016, 81, 5504-5512.

DOI: 10.1021/acs.joc.6b00844 (free Supporting Information)


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Abstract

The reaction of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds efficiently provides α-sulfonated ketones, esters, and amides. TosMIC acts as the sulfonylating agent initiated by a Cu(OTf)2-catalyzed hydration to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of Cs2CO3.

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Key Words

Sulfonylation


ID: J42-Y2016