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Open Access Lithium/Element Exchange as an Efficient Tool for Accessing Atropo-enriched Biaryls via Arynes

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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.

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Keywords: ARYLLITHIUM; ARYNE; BIARYL; BROMINE/LITHIUM INTERCONVERSION; COUPLING; STEREOSELECTIVITY

Document Type: Editorial

Affiliations: 1: CNRS/University of Strasbourg UMR CNRS 7509 – Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France 2: CNRS/University of Strasbourg UMR CNRS 7509 – Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France;, Email: [email protected]

Publication date: February 1, 2016

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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