Metal-Free Oxidative Coupling: Xanthone Formation via Direct Annulation of 2-Aryloxybenzaldehyde using Tetrabutylammonium Bromide as a Promoter in Aqueous Medium

A metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-08, Vol.355 (11-12), p.2191-2196
Main Authors: Rao, Honghua, Ma, Xinyi, Liu, Qianzi, Li, Zhongfeng, Cao, Shengli, Li, Chao-Jun
Format: Article
Language:English
Subjects:
acyl radicals
aldehyde CH bonds
Bonding
Catalysis
Chemical reactions
Joining
metal-free conditions
Organic chemistry
oxidative annulation
Strategy
TBAB-promoted reactions
Tetrabutylammonium bromide
Tolerances
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Summary:A metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron‐donating and electron‐withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300488