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Wiley, Angewandte Chemie, 52(123), p. 12790-12793

DOI: 10.1002/ange.201105105

Wiley, Angewandte Chemie International Edition, 52(50), p. 12582-12585

DOI: 10.1002/anie.201105105

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Highly Twisted Arenes by Scholl Cyclizations with Unexpected Regioselectivity

Journal article published in 2011 by Anirban Pradhan, Pierre Dechambenoit, Harald Bock, Fabien Durola ORCID
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This paper is available in a repository.

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Abstract

Let's twist! The Scholl reaction with quinquephenyl derivatives has been shown to have an unexpectedly strong preference for forming twisted, helicene aromatic polycycles, instead of their flat counterparts. This tendency is so strong that it will overcome even severe steric hindrance, and the procedure can be used in the efficient synthesis of hexa-tert-butylhexabenzotriphenylene from a simple biaryl starting material (see scheme).