Synfacts 2008(3): 0294-0294  
DOI: 10.1055/s-2008-1042728
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Imines and Pyrrolidines via Metal-Free Oxidation of Sulfonamides by Iodine(III)

Contributor(s): Paul Knochel, Andrei Gavryushin
R. Fan*, D. Pu, F. Wen, J. Wu
Fudan University and Shanghai Institute of Organic Chemistry, Shanghai, P. R. of China
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Publication History

Publication Date:
21 February 2008 (online)


The direct oxidation of an sp3 C-H bond is a quite promising, yet still a challenging synthetic transformation. This paper presents a simple and convenient protocol for the metal-free oxidation of benzylic sulfonamides to N-sulfonylimines, and alkyl sulfonamides to N-sulfonylpyrrolidines. The imines can react in situ with a number of nucleophiles or undergo a cycloaddition, giving rise to many useful adducts. This is a very simple synthetic way to 2-alkylpyrrolidines.