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Issue 33, 2017
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Ag(i)-Catalyzed cycloisomerization reactions: synthesis of substituted phenanthrenes and naphthothiophenes

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Abstract

This paper describes silver catalyzed synthesis of substituted phenanthrenes and naphthothiophenes from ortho-alkylated biaryl derivatives via 6-endo-dig intramolecular alkyne–arene coupling. The mechanistic study reveals that 6-endo-dig cyclization proceeds through initial π-coordination of the alkyne unit followed by a Friedel–Crafts-type electrophilic aromatic cyclization at the adjacent arene ring. X-ray crystallographic studies further supported the formation of carbocycles.

Graphical abstract: Ag(i)-Catalyzed cycloisomerization reactions: synthesis of substituted phenanthrenes and naphthothiophenes

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Article information


Submitted
05 Jul 2017
Accepted
22 Jul 2017
First published
24 Jul 2017

Org. Biomol. Chem., 2017,15, 6934-6942
Article type
Paper

Ag(I)-Catalyzed cycloisomerization reactions: synthesis of substituted phenanthrenes and naphthothiophenes

R. K. Saunthwal, A. K. Danodia, K. M. Saini and A. K. Verma, Org. Biomol. Chem., 2017, 15, 6934
DOI: 10.1039/C7OB01646H

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