Synlett 2007(11): 1797-1798  
DOI: 10.1055/s-2007-984504
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

A Fluorinating Hypervalent Iodine(III) Reagent: 4-Iodotoluene Difluoride

Samir Augusto Pino Quintiliano*
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo SP, Brazil
e-Mail: samirpq@gmail.com;
Further Information

Publication History

Publication Date:
25 June 2007 (online)

Introduction

There is a great interest of organic chemists in hypervalent iodine reagents because a wide range of reactions can be performed selectively under mild conditions and, in some cases, catalytically. [1] Fluorinated molecules are highly valuable due to the unique characteristics displayed by the fluorine atom. [2]

4-Iodotoluene difluoride (p-TolIF2, 1) is a hypervalent ­iodine reagent that promotes chemoselective fluorinations avoiding the use of fluorine gas, as well as the expensive xenon difluoride. Several N-fluoro compounds have been developed as stable and effective fluorinating reagents; their preparation, however, generally demands the use of fluorine gas. Compound 1 is usually preferred over its ­iodobenzene difluoride analogue because of easier preparation, purification, and handling.

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