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Highly twisted arenes by Scholl cyclizations with unexpected regioselectivity
Authors:Pradhan Anirban  Dechambenoit Pierre  Bock Harald  Durola Fabien
Affiliation:Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115 Avenue Schweitzer, 33600 Pessac, France.
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).
Keywords:arenes  helicenes  polycycles  regioselectivity  Scholl reaction
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