The Journal of organic chemistry

Synthesis of Benzo-fused Heterocycles by Intramolecular α-Arylation of Ketone Enolate Anions

JF Guastavino, RA Rossi

Index: Guastavino, Javier F.; Rossi, Roberto A. Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 460 - 472

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Citation Number: 18

Abstract

A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular α-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr–CAr coupling led to the formation of five-and six-member benzo-fused heterocycles ( ...

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