Premium
Tin Tetrachloride‐Catalyzed Regiospecific Allylic Substitution of Quinone Monoketals: An Easy Entry to Benzofurans and Coumestans
Author(s) -
Liu Yingjie,
Liu Jingxin,
Wang Mang,
Liu Jun,
Liu Qun
Publication year - 2012
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.201200344
Subject(s) - chemistry , allylic rearrangement , tin , tetrachloride , catalysis , regioselectivity , intramolecular force , cycloaddition , organic chemistry , combinatorial chemistry
A highly regioselective allylic substitution of quinone monoketals with α‐oxoketene dithioacetals is achieved under the catalysis of only tin tetrachloride (1 mol%). The advantages of the reaction, including its simplicity, rapidity, low catalyst loading of inexpensive tin tetrachloride, mild conditions and; in particular, the regiospecificity, is proposed to be due to a pseudo‐intramolecular process. This new synthetic method provides a facile [3+2] cycloaddition route to benzofurans and is highlighted by the synthesis of coumestans.