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Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach

Christof Matt, Frederic Kölblin, Jan Streuff*

*Albert-Ludwigs-Universität Freiburg, Institut für Organische Chemie, Albertstr. 21, 79104 Freiburg, Germany, Email: jan.streuffocbc.uni-freiburg.de

C. Matt, F. Kölblin, J. Streuff, Org. Lett., 2019, 21, 6909-6913.

DOI: 10.1021/acs.orglett.9b02572 (free Supporting Information)


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Abstract

A tethered alkene functionality can be used as a traceless directing group for a zirconium catalyzed reductive cleavage of Csp3 and Csp2 carbon-heteroatom bonds, including C-O, C-N, and C-S bonds. The reaction is especially useful for cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.

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proposed mechanism



Key Words

cleavage of ethers, Schwartz reagent, LAH


ID: J54-Y2019