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J Am Chem Soc. 2008 Aug 27;130(34):11270-1. doi: 10.1021/ja804120r. Epub 2008 Jul 31.

A general and highly selective chelate-controlled intermolecular oxidative Heck reaction.

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  • 1University of Illinois Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.


A novel chelate-controlled intermolecular oxidative Heck reaction is reported that proceeds with a wide range of nonresonance stabilized alpha-olefin substrates and organoboron reagents to afford internal olefin products in good yields and outstanding regio- and E: Z stereoselectivities. Pd-H isomerization, common in many Heck reactions, is not observed under these mild, oxidative conditions. This is evidenced by outstanding E: Z selectivities (>20:1 in all cases examined), no erosion in optical purity for proximal stereogenic centers, and a tolerance for unprotected alcohols. Remarkably, a single metal/ligand combination, Pd/bis-sulfoxide complex 1, catalyzes this reaction over a broad range of coupling partners. Given the high selectivities and broad scope, we anticipate this intermolecular Heck reaction will find heightened use in complex molecule synthesis.

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