Synlett 2007(18): 2924-2925  
DOI: 10.1055/s-2007-990842
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

N-Fluorobenzenesulfonimide [(PhSO2)2NF] - A Neutral N-F-Containing Electrophilic Fluorinating Agent

Amin Rostami*
a Faculty of Chemistry, Bu-Ali Sina University, Hamadan, 6517838683, Iran
b Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran
e-Mail: a_rostami372@yahoo.com;
Further Information

Publication History

Publication Date:
12 October 2007 (online)

Introduction

N-Fluorobenzenesulfonimide [NFSI] is a stable crystalline solid that easy to handle, non-hygroscopic, soluble in most common ethereal and chlorinated solvents, and commercially available. It is a neutral N-F-containing electrophilic fluorinating agent that permits the incorporation of fluorine into neutral and carbanionic nucleophiles ranging from very reactive organometallic species to slightly activated aromatic compounds. [1]

N-Fluorobenzenesulfonimide can be employed in the preparation of aryl (difluoromethylenephosphonates), [2] 20-deoxy-20-fluorocamptothecin, [3] N-fluoro sulfon­amides, [4] 2-amino-5-fluorothiazole hydrochloride [5] and benzylic α,α-difluoronitriles, -tetrazoles, and -sulfonates. [6] When NFSI was associated with chiral palladium complexes an efficient method to catalytic enantioselective fluorination of β-keto esters, [7] and α-cyano acetates [8] was presented.

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