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Carbonylative Coupling of Alkyl Zinc Reagents with Benzyl Bromides Catalyzed by a Nickel/NN 2 Pincer Ligand Complex
Author(s) -
Andersen Thomas L.,
Donslund Aske S.,
Neumann Karoline T.,
Skrydstrup Troels
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710089
Subject(s) - reagent , chemistry , alkyl , catalysis , nickel , ligand (biochemistry) , zinc , carbon monoxide , pincer movement , pincer ligand , combinatorial chemistry , medicinal chemistry , polymer chemistry , organic chemistry , biochemistry , receptor
An efficient catalytic protocol for the three‐component assembly of benzyl bromides, carbon monoxide, and alkyl zinc reagents to give benzyl alkyl ketones is described, and represents the first nickel‐catalyzed carbonylative coupling of two sp 3 ‐carbon fragments. The method, which relies on the application of nickel complexed with an NN 2 ‐type pincer ligand and a controlled release of CO gas from a solid precursor, works well with a range of benzylic bromides. Mechanistic studies suggest the intermediacy of carbon‐centered radicals.