Phenanthrene Synthesis by Eosin Y-Catalyzed, Visible Light- Induced [4+2] Benzannulation of Biaryldiazonium Salts with Alkynes

A metal‐free, visible light‐induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9‐substituted or 9,10‐disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence.

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2012-11, Vol.354 (17), p.3195-3199
Main Authors: Xiao, Tiebo, Dong, Xichang, Tang, Yanchi, Zhou, Lei
Format: Article
Language:English
Subjects:
Alkynes
benzannulation
Catalysis
Catalysts: preparations and properties
Chemistry
Condensed benzenic and aromatic compounds
diazonium salts
Exact sciences and technology
Free radicals chemistry
General and physical chemistry
Organic chemistry
phenanthrenes
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Preparations and properties
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
visible light
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Description
Summary:A metal‐free, visible light‐induced [4+2] benzannulation of biaryldiazonium salts with alkynes was developed. With eosin Y as photoredox catalyst, a variety of 9‐substituted or 9,10‐disubstituted phenanthrenes were obtained via a cascade radical addition and cyclization sequence.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201200569