Alkynes as Linchpins for the Additive Annulation of Biphenyls: Convergent Construction of Functionalized Fused Helicenes | Zendy

Mohamed Rana K. | Zendy; Mondal Sayantan | Zendy; Guerrera Joseph V. | Zendy; Eaton Teresa M. | Zendy; AlbrechtSchmitt Thomas E. | Zendy; Shatruk Michael | Zendy; Alabugin Igor V. | Zendy

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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.

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