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

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.

SUBMITTER: Srinivas HD

PROVIDER: S-EPMC4084837 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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

Srinivas Harathi D HD Zhou Qi Q Watson Mary P MP

Organic letters 20140613 13

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 ...[more]

PMID: 24927013

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