Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
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Buchwald_Synthesis of heteroaryl.pdf
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Author(s)
Colombe, James Robert
DeBergh, John Robbins
Buchwald, Stephen Leffler
Date Issued
June 2015
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.
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Final published version
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.5b01540
