Nucleophile-catalyzed, facile, and highly selective C–H activation of fluoroform with Pd (II)

S Takemoto, VV Grushin

Index: Lishchynskyi, Anton; Grushin, Vladimir V. Journal of the American Chemical Society, 2013 , vol. 135, # 34 p. 12584 - 12587

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Citation Number: 19

Abstract

Exceedingly facile (23° C) and chemoselective H-CF3 activation with [(dppp) Pd (Ph)(OH)] in the presence of a Lewis base promoter such as n-Bu3P leads to Pd-CF3 bond formation in nearly quantitative yield. A combined experimental and computational study points to a new mechanism that involves H-bonding Pd-O (H)··· H-CF3 and nucleophilic attack of the promoter on the metal, followed by a push-pull-type collapse of the resultant five- ...