Couplings of benzylic halides mediated by titanocene chloride: synthesis of bibenzyl derivatives

Alejandro F Barrero; M Mar Herrador; José F Quílez del Moral; Pilar Arteaga; Mohammed Akssira; Fadwa El Hanbali; Jesús F Arteaga; Horacio R Diéguez; Elena M Sánchez

doi:10.1021/jo062492p

Couplings of benzylic halides mediated by titanocene chloride: synthesis of bibenzyl derivatives

J Org Chem. 2007 Mar 16;72(6):2251-4. doi: 10.1021/jo062492p. Epub 2007 Feb 20.

Authors

Alejandro F Barrero¹, M Mar Herrador, José F Quílez del Moral, Pilar Arteaga, Mohammed Akssira, Fadwa El Hanbali, Jesús F Arteaga, Horacio R Diéguez, Elena M Sánchez

Affiliation

¹ Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Avda. Fuentenueva, 18071 Granada, Spain. [email protected]

PMID: 17309310
DOI: 10.1021/jo062492p

Abstract

Titanocene monochloride catalyzes the homocoupling of benzylic halides and benzylic gem-dibromides to give the corresponding bibenzyl and stilbenyl systems. Exposure of benzylic bromides to Ti(III) in the presence of aldehydes gave rise to the Barbier-type products. Examples of the utility of the herein described processes are included.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemical synthesis*
Bibenzyls / chemical synthesis*
Catalysis
Organometallic Compounds / chemistry
Stilbenes / chemical synthesis*
Titanium

Substances

Benzene Derivatives
Bibenzyls
Organometallic Compounds
Stilbenes
titanocene
Titanium