Oxygen-Promoted Pd(II) Catalysis for the Coupling of Organoboron Compounds and Olefins

Young Chun Jung, Rajesh Kumar Mishra, Cheol Hwan Yoon and Kyung Woon Jung*

*Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, Email: kwjungusc.edu

Y. C. Jung, R. K. Mishra, C. H. Yoon, K. W. Jung, Org. Lett., 2003, 5, 2231-2234.

DOI: 10.1021/ol034458s (free Supporting Information)

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Abstract

A mild and efficient Pd(II) catalysis leads to the formation of carbon-carbon bonds between various organoboron compounds and alkenes. The resultant Pd(0) species is reoxidized by molecular oxygen to Pd(II). This protocol promotes the desired Pd(II) catalysis, whereas the competing Pd(0) pathways (Heck or Suzuki) are retarded.

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proposed mechanism

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

K. S. Yoo, C. H. Yoon, J. W. Jung, J. Am. Chem. Soc., 2006, 128, 16348-16393.

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Key Words

Boronic Acids, Esters, Coupling, Olefins, Alkenylation, Oxygen

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ID: J54-Y2003-460