title: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
authors.forename: Harathi D
authors.initials: HD
authors.lastname: Srinivas
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhou
authors.forename: Mary P
authors.initials: MP
authors.lastname: Watson
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010421:Pentanoic Acids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D006841:Hydrocarbons, Aromatic; D010421:Pentanoic Acids; D009532:Nickel; C005566:pivalic acid