Computational methods were employed to study the Cu(I)-catalyzed thiol esters and boronic acids cross-coupling reaction previously reported by Liebeskind and co-workers (J. Am. Chem. Soc. 2007  , 129, 15734-15735). A dimeric complex containing a Cu2O2-core has been proposed to be the active species.In the first part of this presentation we will describe factors controlling stability of different isomers, such as LCuII[�-?2:?2-peroxo]CuIIL, LCuII[trans-�-1,2-peroxo]CuIIL and LCuIII[�-oxo]2CuIIIL, of the active species. Computations show that all of these isomers are thermodynamic and kinetically accessible.In the second part of this presentation the key transition-state structures associated with the transmetallation process and the formation of the two experimentally observed products, ketone and thioether, will be discussed.

Mechanistic details of aerobic Cu(I)-catalyzed thiol and boronic acid cross-coupling reaction

244th National Meeting (2012)

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