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Carbenoid insertions into benzylic C-H bonds with heterogeneous copper catalysts

AuthorsFraile, José M. ; Mayoral, José A. ; Muñoz, Ana; Santafé-Valero, Jorge
KeywordsCarbene insertion
Heterogeneous catalysis
Copper catalysts
Benzylic insertion
Issue Date2013
CitationTetrahedron 69(35): 7360-7364 (2013)
AbstractThe copper complexes with bis(oxazoline) or azabis(oxazoline) ligands, once supported on laponite clay by electrostatic interactions, are able to catalyze the insertion of carbenoids in benzylic C-H bonds. In contrast with rhodium catalysts, they are more active with tertiary than with secondary bonds, through a similar mechanism as shown by Hammet correlation. Enantioselectivities are only moderate, with values up to 50% ee. The immobilized catalysts are partially recoverable and the best results are obtained in the case of reactions with high chemoselectivity. © 2013 Elsevier Ltd. All rights reserved.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2013.06.088
Identifiersdoi: 10.1016/j.tet.2013.06.088
issn: 0040-4020
Appears in Collections:(ISQCH) Artículos
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