Electronic effects on the selectivity of Pd-catalyzed C-N bond-forming reactions using biarylphosphine ligands: The competitive roles of amine binding and acidity

Angewandte Chemie - International Edition

Volumn 46, Issue 38, 2007, Pages 7232-7235

  Biscoe, Mark R ^a   Barder, Timothy E ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Amination; Chemoselectivity; Homogeneous catalysis; Palladium; Phosphanes

Indexed keywords

AMINES; CATALYST ACTIVITY; CATALYST SELECTIVITY; CHEMICAL BONDS; PALLADIUM;

CATALYTIC ARYLATION; CHEMOSELECTIVITY; CROSS-COUPLING REACTIONS; ELECTRONIC EFFECTS; PHOSPHANES;

REACTION KINETICS;

AMINE; CARBON; CYCLOHEXANE DERIVATIVE; LIGAND; NITROGEN; ORGANOMETALLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

AMINES; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANES; LIGANDS; NITROGEN; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES;

EID: 34948848248     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702122     Document Type: Article

References (25)

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24. Preliminary calculations suggest that arylations are less selective for primary amines than for secondary amines because of reversible deprotonation and slow reductive elimination. See the Supporting Information for further details.
25. Because we focus herein on the influence of electronic effects on selectivity, a through investigation of steric effects was not performed. A more comprehensive study of the influence of steric effects on selectivity will be reported elsewhere.