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Issue 9, 2012
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Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents

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Abstract

A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl)arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.

Graphical abstract: Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents

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Article information


Submitted
02 Apr 2012
Accepted
04 Jun 2012
First published
13 Jun 2012

New J. Chem., 2012,36, 1769-1773
Article type
Paper

Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents

G. Liu, S. Mori, X. Wang, S. Noritake, E. Tokunaga and N. Shibata, New J. Chem., 2012, 36, 1769
DOI: 10.1039/C2NJ40255F

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