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Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Tomas Javorskis and Edvinas Orentas*

*Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania, Email: edvinas.orentaschf.vu.lt

T. Javorskis, E. Orentas, J. Org. Chem., 2017, 82, 13423-13439.

DOI: 10.1021/acs.joc.7b02507 (free Supporting Information)


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Abstract

For chemoselective acidic hydrolysis of N-arylsulfonamides with trifluoromethanesulfonic acid, a near-stoichiometric amount of the acid was found to be sufficient to deprotect various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products.


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Key Words

Deprotection of Toluenesulfonamides


ID: J42-Y2017