Journal of the American Chemical Society 2012-04-18

Copper-mediated aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides at room temperature.

Qingqing Qi, Qilong Shen, Long Lu

Index: J. Am. Chem. Soc. 15th ed., 134 , 6548-6551, (2012)

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Abstract

A Cu-mediated ligandless aerobic fluoroalkylation of arylboronic acids under mild conditions is described for the first time. The reaction tolerates a wide range of functional groups, allowing for further transformation. Mechanistic studies suggest that [R(f)Cu] is the active Cu species that forms the desired perfluoroalkylarenes and that [R(f)Cu] is generated from [PhCu] by either an oxidative addition/reductive elimination mechanism or nucleophilic substitution via a halogen "ate" intermediate.© 2012 American Chemical Society