Tin Tetrachloride‐Catalyzed Regiospecific Allylic Substitution of Quinone Monoketals: An Easy Entry to Benzofurans and Coumestans | Zendy

Liu Yingjie | Zendy; Liu Jingxin | Zendy; Wang Mang | Zendy; Liu Jun | Zendy; Liu Qun | Zendy

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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.

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