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Dioxygen-Promoted Regioselective Oxidative Heck Arylations of Electron-Rich Olefins with Arylboronic Acids

Murugaiah M. S. Andappan, Peter Nilsson, Henrik von Schenck and Mats Larhed*

*Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, BMC, Uppsala University, Box-574, SE-751 23 Uppsala, Sweden, Email: matsorgfarm.uu.se

M. M. S. Andappan, P. Nilsson, H. v. Schenck, M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.

DOI: 10.1021/jo049434t (free Supporting Information)



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Abstract

Arylations of electron-rich heteroatom-substituted olefins were performed with electron-rich arylboronic acids via palladium(II) catalysis. This mild protocol, which offers access to functionalized enamides, exploits oxygen gas for reoxidation and a stable 1,10-phenanthroline bidentate ligand to promote the palladium(II) regeneration and to control the regioselectivity.

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Key Words

Heck Reaction, Microwave Synthesis, Oxygen, Olefination, Enamides


ID: J42-Y2004-610