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Trichloromethanesulfonyl Chloride: A Chlorinating Reagent for Aldehydes

Ciril Jimeno, Lidong Cao and Philippe Renaud*

*Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland, Email: philippe.renauddcb.unibe.ch

C. Jimeno, L. Cao, P. Renaud, J. Org. Chem., 2016, 81, 1251-1255.

DOI: 10.1021/acs.joc.5b02453 (free Supporting Information)


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Abstract

The use of the commercially available trichloromethanesulfonyl chloride enables an efficient α-chlorination of aldehydes, including a catalytic asymmetric version, under very mild reaction conditions. This chlorinating reagent facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.

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Key Words

α-chlorination, chlorohydrins, sodium borohydride


ID: J42-Y2016