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Synlett 2006(9): 1283-1294
DOI: 10.1055/s-2006-939728
DOI: 10.1055/s-2006-939728
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Discovery and Understanding of Transition-Metal-Catalyzed Aromatic Substitution Reactions
Further Information
Received
5 January 2006
Publication Date:
22 May 2006 (online)
Publication History
Publication Date:
22 May 2006 (online)
Abstract
This article presents studies on the development of cross-coupling reactions of aryl halides and sulfonates with amines, alkoxides, and various enolates. Emphasis is placed on the process of developing new catalysts with mechanistic information gained in the author’s laboratory.
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1 Introduction
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2 Early Reaction Development
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3 New Catalyst Developments
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4 Mechanism of the Cross-Coupling Processes
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5 Mechanism of Oxidative Addition
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6 Reductive Elimination of Amines
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7 Stable Palladium Catalysts for Coupling of Primary Amines
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8 Guidelines for Catalyst Selection
Key words
cross-coupling - palladium - amination - arylation - mechanism
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References and Notes
For a review of our work on the reductive elimination to form carbon-nitrogen and carbon-oxygen bonds, see reference 10.
54Our original work on the catalytic process led to the conclusion that the immediate product of the C-N bond-forming step [Pd(BINAP)(NArRR")], reacts with free ligand to regenerate [Pd(BINAP)2] faster than the amine dissociates to generate [Pd(BINAP)] and that [Pd(BINAP)2] lies directly on the catalytic cycle. We recently remeasured kinetic data on the order of the catalytic process in bromoarene and ligand and our corrected data imply that [Pd(BINAP)(NArRR")] dissociates the amine to form [Pd(BINAP)] faster than it reacts with the free ligand and that [Pd(BINAP)2] lies off the cycle as shown in Scheme [4] . These data are presented in reference 62.