Organic Letters 2014-07-03

Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Harathi D Srinivas, Qi Zhou, Mary P Watson

Index: Org. Lett. 16(13) , 3596-9, (2014)

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Abstract

We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.