title: Lithium/Element Exchange as an Efficient Tool for Accessing Atropo-enriched Biaryls via Arynes.
abstract: This account documents the development of transition metal-free, aryne-mediated aryl-aryl coupling, the 'ARYNE coupling', which began in 2001 in Lausanne. ortho,ortho'-Di-, tri- and even tetrasubstituted biphenyls have now become accessible on a multi-gram scale. The reaction is perfectly regioselective and the obtained polybromobiphenyls can be submitted to regioselective bromine/lithium interconversions. The access to enantiopure biphenyls is now possible using enantiopure sulfoxides as chiral auxiliaries, which allow for subsequent chemoselective sulfoxide/metal exchange on each atropo-diastereoisomer with configurational stability of the intermediate biaryllithiums. Direct atropo-diastereoselective ARYNE coupling has been reported more recently.
authors.affiliation: CNRS/University of Strasbourg UMR CNRS 7509 - Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France.
authors.forename: Armen
authors.initials: A
authors.lastname: Panossian
authors.affiliation: CNRS/University of Strasbourg UMR CNRS 7509 - Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France. frederic.leroux@unistra.fr.
authors.forename: Frédéric R
authors.initials: FR
authors.lastname: Leroux
mesh_terms: D001713:Biphenyl Compounds / Q000737:chemistry; D001966:Bromine / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry
chemical_list: D001713:Biphenyl Compounds; D013454:Sulfoxides; D008094:Lithium; D001966:Bromine