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Addition of Arylboronic Acids to Arylpropargyl Alcohols en Route to Indenes and Quinolines

Jane Panteleev, Richard Y. Huang, Erica K. J. Lui and Mark Lautens*

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

J. Panteleev, R. Y. Huang, E. K. J. Lui, M. Lautens, Org. Lett., 2011, 13, 5314-5317.

DOI: 10.1021/ol202176g (free Supporting Information)



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Abstract

A regio- and stereoselective rhodium-catalyzed reaction of propargylic alcohols with boronic acids enables the synthesis of trisubstituted allylic alcohols. The utility of these synthons is demonstrated in a convenient synthesis of indenes and quinolines.

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Key Words

Arylation, Friedel-Crafts Alkylation, Indenes


ID: J54-Y2011-2940