Organic Chemistry Portal



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:

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

DOI: 10.1021/acs.orglett.9b02572

see article for more reactions


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.

see article for more examples

proposed mechanism

Key Words

cleavage of ethers, Schwartz reagent, LAH

ID: J54-Y2019