Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate

Author(s)
Colombe, James Robert; DeBergh, John Robbins; Buchwald, Stephen Leffler
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Abstract
A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.
Date issued
2015-06
URI
http://hdl.handle.net/1721.1/104057
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Colombe, James R., J. Robb DeBergh, and Stephen L. Buchwald. “Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.” Organic Letters 17, no. 12 (June 19, 2015): 3170–3173. © 2015 American Chemical Society.
Version: Final published version
ISSN
1523-7060
1523-7052
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