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

Authors

  • Armen Panossian CNRS/University of Strasbourg UMR CNRS 7509 – Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France
  • Frédéric R. Leroux CNRS/University of Strasbourg UMR CNRS 7509 – Laboratoire de Chimie, Moléculaire, ECPM, 25 Rue Becquerel, 67087 Strasbourg Cedex 2, France;, Email: frederic.leroux@unistra.fr

DOI:

https://doi.org/10.2533/chimia.2016.43

Keywords:

Aryllithium, Aryne, Biaryl, Bromine/lithium interconversion, Coupling, Stereoselectivity

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.

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Published

2016-02-24

How to Cite

[1]
A. Panossian, F. R. Leroux, Chimia 2016, 70, 43, DOI: 10.2533/chimia.2016.43.

Issue

Section

Scientific Articles