Lithium/Element Exchange as an Efficient Tool for Accessing Atropo-enriched Biaryls via Arynes
Keywords:Aryllithium, Aryne, Biaryl, Bromine/lithium interconversion, Coupling, Stereoselectivity
AbstractThis 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.
How to Cite
A. Panossian, F. R. Leroux, Chimia 2016, 70, 43, DOI: 10.2533/chimia.2016.43.
Copyright (c) 2016 Swiss Chemical Society
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