Exploiting Boron–Zinc Transmetallation for the Arylation of Benzyl Halides: What are the Reactive Species?

RB Bedford, NJ Gower, MF Haddow…

Index: Bedford, Robin B.; Carter, Emma; Cogswell, Paul M.; Gower, Nicholas J.; Haddow, Mairi F.; Harvey, Jeremy N.; Murphy, Damien M.; Neeve, Emily C.; Nunn, Joshua Angewandte Chemie - International Edition, 2013 , vol. 52, # 4 p. 1285 - 1288

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Citation Number: 23

Abstract

Following pioneering work by Bolm and co-workers,[1] B–Zn transmetallation reactions between arylboronic acids and diethylzinc have been exploited in a range of asymmetric nucleophilic addition reactions to carbonyl and related compounds in the presence of catalytic amounts of chiral ligands and, in some cases, transition-metal catalysts.[2–7] These reactions usually require a pre-activation step, in which ArB (OH) 2 and Et2Zn are heated ...