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Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization

An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to b...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-09, Vol.2012 (27), p.5381-5388
Main Authors: Raji Reddy, Chada, Krishna, Gaddam, Kavitha, Nerella, Latha, Bellamkonda, Shin, Dong-Soo
Format: Article
Language:English
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Summary:An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to be built. The procedure consists of one‐pot nucleophilic substitution, TBS‐deprotection, and exo‐dig cycloisomerization. A one‐pot method for the synthesis of diversely 2,3‐disubstituted benzofurans from propargylic alcohols is described. The strategy involves acid‐catalyzed nucleophilic substitution followed by TBAF‐mediated desilylative exo‐dig‐oxacycloisomerization.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200708