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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 22
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Original Articles

Novel One-Pot Synthesis of 3-Phenylnaphtho[2,3-b]furan and 3-Phenylbenzofurans Under Microwave Irradiation and Solvent-Free Conditions

, , &
Pages 4079-4087 | Received 01 Dec 2008, Published online: 16 Oct 2009
 

Abstract

A one-pot synthesis of functionalized benzofurans has been developed via O-alkylation, carbon–carbon coupling/cyclization, and dehydration/olefination tandem reactions from phenacyl bromide and phenols under microwave irradiation and solvent-free conditions in the presence of mineral-supported reagent and inorganic base. The best selectivity for forming benzofuran product has been achieved with Na2CO3 as a base. The order of activity of inorganic base is as follows: K2CO3 > NaHCO3 > Na2CO3 > KHCO3 > Na2SO3 > KOH > K3PO4 > NaOH > KH2PO4 > KOAc. This novel synthesis features three new bonds and one ring system assembled in a single step.

ACKNOWLEDGMENT

We are grateful for the financial support of the National Natural Science Foundation of China (NSFC 20773055 and 20021001).

Notes

a Isolated yield.

Note. Reaction conditions: phenacyl bromide, 995 mg (5 mmol); naphthalene (5 mmol); inorganic base (2.5 mmol); and Al2O3 (5.2 g).

a Isolated yield.

Note. Reaction conditions: phenacyl bromide (5 mmol); naphthalene (5 mmol); K2CO3; 350 mg (2.5 mmol); MSR (5.2 g).

a Isolated yield.

Note. Reaction conditions: phenacyl bromide (5 mmol); naphthalene (5 mmol); Al2O3 (5.2 g).

a Isolated yield.

b CEM Discover instrument using an open vessel.

Note. Reaction conditions: phenacyl bromide, 995 mg (5 mmol); naphthalene (5 mmol); Al2O3 (5.2 g); K2CO3, 350 mg (2.5 mmol).

a Isolated yield.

Note. Reaction conditions: phenacyl bromide, 995 mg (5 mmol); phenols (5 mmol); Al2O3 (3 equivalents of substrate, w/w).

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