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Abstract
A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine but not 2-chloropyridine and other α-halo-N-heterocycles. Further investigations revealed that
chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation ofstable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the
corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of
Grignard reagents.
Supplementary materials
Title
SUPPORTING INFORMATION FOR Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles
Description
Synthesis of new complexes; X-ray crystallography data; GC-FID data; kinetic data; and computational data.
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