Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines | Zendy

Harathi D. Srinivas | Zendy; Qi Zhou | Zendy; Mary P. Watson | Zendy

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Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines

Author(s) -

Harathi D. Srinivas,

Qi Zhou,

Mary P. Watson

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5016724

Subject(s) - allylic rearrangement , chemistry , catalysis , nickel , regioselectivity , combinatorial chemistry , ligand (biochemistry) , reagent , scope (computer science) , functional group , stereochemistry , organic chemistry , receptor , biochemistry , polymer , computer science , programming language

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.

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