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

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

Organic letters (2014-06-14)

Harathi D Srinivas, Qi Zhou, Mary P Watson

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.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Nickel, powder, <50 μm, 99.7% trace metals basis

Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

Raney^®-Nickel, W.R. Grace and Co. Raney^® 2800, slurry, in H₂O, active catalyst

Sigma-Aldrich

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Sigma-Aldrich

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Nickel, foam, 300x300mm, thickness 1.6mm, bulk density 0.45g/cm³, porosity 95%, 95%