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A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl Chlorides

Brett P. Fors, Donald A. Watson, Mark R. Biscoe and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

B. P. Fors, D. A. Watson, M. R. Biscoe, S. L. Buchwald, J. Am. Chem. Soc., 2008, 130, 13552-13554.

DOI: 10.1021/ja8055358 (free Supporting Information)


Abstract

A catalyst system based on a new biarylmonophosphine ligand shows excellent reactivity for C-N cross-coupling reactions. This catalyst system enables the use of aryl mesylates as a coupling partner and permits a highly selective monoarylation of an array of primary aliphatic amines and anilines at low catalyst loadings and with fast reaction times.

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Water-Mediated Catalyst Preactivation: An Efficient Protocol for C-N Cross-Coupling Reactions

B. P. Fors, P. Krattiger, E. Strieter, S. L. Buchwald, Org. Lett., 2008, 10, 3505-3508.


Key Words

Buchwald-Hartwig Coupling, Arylamines


ID: J48-Y2008-2830