Oxidative Palladium(II) Catalysis:  A Highly Efficient and Chemoselective Cross-Coupling Method for Carbon−Carbon Bond Formation under Base-Free and Nitrogenous-Ligand Conditions

Kyung Soo Yoo, Cheol Hwan Yoon, and Kyung Woon Jung*
Contribution from the Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661
J. Am. Chem. Soc., 2006, 128 (50), pp 16384–16393
DOI: 10.1021/ja063710z
Publication Date (Web): November 30, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kwjung@usc.edu

Abstract

Abstract Image

We report herein the development of a general and mild protocol of oxygen-promoted Pd(II) catalysis resulting in the selective cross-couplings of alkenyl- and arylboron compounds with various olefins. Unlike most cross-coupling reactions, this new methodology works well even in the absence of bases, consequently averting undesired homo-couplings. Nitrogen-based ligands including dimethyl-phenanathroline enhance reactivities and offer a highly efficient and stereoselective methodology to overcome challenging substrate limitations. For instance, oxidative palladium(II) catalysis is effective with highly substituted alkenes and cyclic alkenes, which are known to be incompatible with other known catalytic conditions. Most examined reactions progressed smoothly to completion at low temperatures and in short times. These interesting results provide mechanistic insights and utilities for a new paradigm of palladium catalytic cycles without bases.

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History

  • Published In Issue December 20, 2006
  • Received May 26, 2006

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