Issue 33, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2017
Accepted
22 Jul 2017
First published
24 Jul 2017

Org. Biomol. Chem., 2017,15, 6934-6942

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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