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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 2
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Original Articles

Simple, Convenient, and Efficient Synthesis of 2-Aryl-substituted Benzo[b]furans

, , , , &
Pages 197-204 | Received 18 Mar 2007, Published online: 22 Dec 2008
 

Abstract

A simple, convenient, and efficient one-pot method for the preparation of benzofuran is reported. Sonogashira coupling reaction of aryl iodides with 2-methyl-3-butyn-2-ol was used as an acetylene source in the presence of Pd(PPh3)2Cl2 and CuI. Deprotection of the acetylene moiety in the same pot using a strong base and the second Sonogashira coupling/cyclization of and substituted o-iodophenols led to the formation of the appropriate benzo[b]furans. These protocols also can be used in the synthesis of natural products and indoles.

ACKNOWLEDGMENT

The authors thank the State Key Laboratory of Applied Organic Chemistry for financial support.

Notes

a Reacted in a 110 °C oil bath or at the boiling point of the solvent under an argon atmosphere for 24 h.

b No benzofuran product was detected by TLC.

a o-Iodophenols were prepared according to the literature procedure Ref.[ Citation 13 ].

a 0.02 mmol of Pd(OAc)2 and 0.04 mmol of PPh3 were used instead of Pd(PPh3)2Cl2 and reacted at 50 °C in the first step.

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