Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines

A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis­[bis­(dimethyl­amino)­phosphino]­ferrocene “DMAPF”...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-08, Vol.139 (31), p.10613-10616
Main Authors: Keylor, Mitchell H, Niemeyer, Zachary L, Sigman, Matthew S, Tan, Kian L
Format: Article
Language:English
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Summary:A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis­[bis­(dimethyl­amino)­phosphino]­ferrocene “DMAPF”, a readily available yet previously unutilized diphosphine, as a uniquely effective ligand for this transformation.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b05409