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Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands

Matthew G. Lauer, Mallory K. Thompson and Kevin H. Shaughnessy*

*Department of Chemistry, The University of Alabama, P.O. Box 870336, Tuscaloosa, Alabama 35487-0336, United States, Email:

M. G. Lauer, M. K. Thompson, K. H. Shaughnessy, J. Org. Chem., 2014, 79, 10837-10848.

DOI: 10.1021/jo501840u (free Supporting Information)

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Neopentyl phosphine ligands promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of 2,3-dihydrofuran di-tert-butylneopentylphosphine (DTBNpP) promotes isomerization to a much greater extent than trineopentylphosphine (TNpP). A similar complementary product selectivity is seen in the Heck coupling of cyclopentene.

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Key Words

2,3-dihydrofurans, 2,5-dihydrofurans

ID: J42-Y2014