Open AccessLithium/Element Exchange as an Efficient Tool for Accessing Atropo-enriched Biaryls via Arynes
Author(s) -
Armen Panossian,
Frédéric R. Leroux
Publication year - 2016
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2016.43
Subject(s) - aryne , enantiopure drug , regioselectivity , aryl , chemistry , diastereomer , lithium (medication) , combinatorial chemistry , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , medicine , alkyl , endocrinology
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.