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Metal‐Free Oxidative Coupling: Xanthone Formation via Direct Annulation of 2‐Aryloxybenzaldehyde using Tetrabutylammonium Bromide as a Promoter in Aqueous Medium
Author(s) -
Rao Honghua,
Ma Xinyi,
Liu Qianzi,
Li Zhongfeng,
Cao Shengli,
Li ChaoJun
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300488
Subject(s) - chemistry , xanthone , intramolecular force , aldehyde , annulation , bromide , aqueous solution , photochemistry , aqueous medium , metal , oxidative coupling of methane , oxidative phosphorylation , organic chemistry , medicinal chemistry , catalysis , biochemistry
A metal‐free intramolecular annulation of 2‐aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde CH bond and aromatic CH 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.