Nickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols Enabled by Bidentate N-Heterocyclic Carbene (NHC)/Phosphine Ligands
ACS Catalysis2017Vol. 8(1), pp. 86–89
Citations Over TimeTop 10% of 2017 papers
S. Hadi Nazari, Jefferson E. Bourdeau, Michael R. Talley, Gabriel A. Valdivia‐Berroeta, Stacey J. Smith, David J. Michaelis
Abstract
Cross couplings between simple allylic alcohols and aryl and vinyl boronic acids are efficiently catalyzed by nickel(0) catalysts and bidentate N-heterocyclic carbene/phosphine ligands. The bidentate nature of the ligand is shown to extend catalyst lifetime and enable high yields of the corresponding cross-coupling products. X-ray crystallography confirms the bidentate nature of the ligand scaffold. Multistep cross coupling-alkene/alkyne insertions reactions are also conducted and the bidentate nature of the substrate makes the pendant phosphine of the ligand unnecessary.
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