Angewandte Chemie. International edition in English 2011-12-23

Highly twisted arenes by Scholl cyclizations with unexpected regioselectivity.

Anirban Pradhan, Pierre Dechambenoit, Harald Bock, Fabien Durola

Index: Angew. Chem. Int. Ed. Engl. 52th ed., 50 , 12582-12585, (2011)

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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).Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.