Nucleophile-Catalyzed, Facile, and Highly Selective C−H Activation of Fluoroform with Pd(II)

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-coordinate Pd(II) intermediate via a polar transition state.

Nucleophile-Catalyzed, Facile, and Highly Selective C?H Activation of Fluoroform with Pd(II)

S. Takemoto, V. V. Grushin

J. Am. Chem. Soc. 2013, 135, 16837-16840
DOI: Go to the journal

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