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J Am Chem Soc. 2017 Aug 9;139(31):10613-10616. doi: 10.1021/jacs.7b05409. Epub 2017 Jul 27.

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

Author information

1
Global Discovery Chemistry, Novartis Institutes for Biomedical Research , 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
2
Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.

Abstract

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.

PMID:
28715180
DOI:
10.1021/jacs.7b05409

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