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Rhodium-Catalyzed Tandem Cyclization: Formation of 1H-Indenes and 1-Alkylideneindans from Arylboronate Esters in Aqueous Media

Mark Lautens* and Tzvetelina Marquardt

*Davenport Chemical Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, Email: mlautenschem.utoronto.ca

M. Lautens, T. Marquardt, J. Org. Chem., 2004, 69, 4607-4614.

DOI: 10.1021/jo049722p


Abstract

Arylboronate esters bearing a pendant Michael-type acceptor olefin undergo a transmetalation with a rhodium-based catalytic complex. These organorhodium intermediates can cyclize onto nonterminal acetylenes in good to excellent yields.

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Key Words

Rhodium, Catalysis, Indenes


ID: J42-Y2004-580