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Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes
Author(s) -
Mohamed Rana K.,
Mondal Sayantan,
Guerrera Joseph V.,
Eaton Teresa M.,
AlbrechtSchmitt Thomas E.,
Shatruk Michael,
Alabugin Igor V.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606330
Subject(s) - planarity testing , annulation , substituent , chemistry , sequence (biology) , solid state , stereochemistry , combinatorial chemistry , crystallography , organic chemistry , catalysis , biochemistry
A new approach to fused helicenes is reported, where varied substituents are readily incorporated in the extended aromatic frame. From the alkynyl precursor, the final helical compounds are obtained under mild conditions in a two‐step process, in which the final C−C bond is formed via a photochemical cyclization/ dehydroiodination sequence. The distortion of the π‐system from planarity leads to unusual packing in the solid state. Computational analysis reveals that substituent incorporation perturbs geometries and electronic structures of these nonplanar aromatics.