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  • Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Angewandte Chemie (International ed. in English) (2015-06-03)
Nathaniel H Park, Ekaterina V Vinogradova, David S Surry, Stephen L Buchwald
ABSTRACT

In Pd-catalyzed C-N cross-coupling reactions, α-branched secondary amines are difficult coupling partners and the desired products are often produced in low yields. In order to provide a robust method for accessing N-aryl α-branched tertiary amines, new catalysts have been designed to suppress undesired side reactions often encountered when these amine nucleophiles are used. These advances enabled the arylation of a wide array of sterically encumbered amines, highlighting the importance of rational ligand design in facilitating challenging Pd-catalyzed cross-coupling reactions.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
APhos Pd G4, 95%
Sigma-Aldrich
(R)-TolBINAP Pd G4, 95%
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Bis(3,5-bis(trifluoromethyl)phenyl)(2′,6′-bis(dimethylamino)-3,6-dimethoxybiphenyl-2-yl)phosphine, ≥95%
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(t-Bu)PhCPhos Pd G4, 95%
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N-XantPhos Pd G4, 95%
Sigma-Aldrich
DPPF Pd G4, 95%