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

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...

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Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (12), p.3170-3173
Main Authors: Colombe, James R, DeBergh, J. Robb, Buchwald, Stephen L
Format: Article
Language:English
Subjects:
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Hydrocarbons, Chlorinated - chemistry
Indicators and Reagents - chemistry
Letter
Molecular Structure
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
Sulfonic Acids - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01540