Mechanistic and Computational Studies of Oxidatively-Induced Aryl− CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation

ND Ball, JB Gary, Y Ye, MS Sanford

Index: Ball, Nicholas D.; Gary, J. Brannon; Ye, Yingda; Sanford, Melanie S. Journal of the American Chemical Society, 2011 , vol. 133, # 19 p. 7577 - 7584

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Citation Number: 128

Abstract

This article describes the rational design of first generation systems for oxidatively induced Aryl− CF3 bond-forming reductive elimination from PdII. Treatment of (dtbpy) PdII (Aryl)(CF3)(dtbpy= di-tert-butylbipyridine) with NFTPT (N-fluoro-1, 3, 5-trimethylpyridinium triflate) afforded the isolable PdIV intermediate (dtbpy) PdIV (Aryl)(CF3)(F)(OTf). Thermolysis of this complex at 80° C resulted in Aryl− CF3 bond-formation. Detailed experimental and ...