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Metal-free carbon-carbon bond-forming reductive coupling between boronic acids and tosylhydrazones

José Barluenga*, María Tomás-Gamasa, Fernando Aznar & Carlos Valdés*

*Instituto Universitario de Química Organometálica "Enrique Moles", Unidad Asociada al C.S.I.C. Universidad de Oviedo, Julián Clavería, 8, E-33006 Oviedo, Spain, Email:,

J. Barluenga, M. Tomás-Gamasa, F. Aznar, C. Valdés, Nat. Chem., 2009, 1, 494-499.

DOI: 10.1038/nchem.328


A metal-free carbon-carbon bond-forming coupling between tosylhydrazones and boronic acids is very general and functional-group tolerant. As the required tosylhydrazones are easily generated from carbonyl compounds, it can be seen as a reductive coupling of carbonyls, a process of high synthetic relevance that requires several steps using other methodologies.

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proposed possible mechanistic pathways

Key Words

Diarylmethanes, Benzylation

ID: JXX-Y2009-0030