Cyclic Diaryl λ-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions.

Org Lett

Laboratoire d'Innovation Moléculaire et Applications (UMR CNRS 7042), Université de Strasbourg/Université de Haute Alsace, ECPM, 25 rue Becquerel, 67087 Strasbourg, France.

Published: December 2021

Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2',3',4-substituted biaryls via pericyclic reactions of cyclic diaryl λ-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.

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http://dx.doi.org/10.1021/acs.orglett.1c03278DOI Listing

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