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Published on: May 25, 2016
Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach
Christof Matt1, Frederic Kölblin1, Jan Streuff1
1Albert-Ludwigs-Universität Freiburg, Institut für Organische Chemie, Albertstr. 21, 79104 Freiburg, Germany.
Abstract:
A zirconium catalyzed reductive cleavage of Csp and Csp carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization of the catalyst further enables the cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.
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