4.7 Article

Phase-Transfer-Catalyzed Intramolecular Cyclization of ortho-Alkynyl Phenyl Ether Derivatives for Synthesis of 2,3-Disubstituted Benzo[b]furans

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 2-3, Pages 351-356

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900649

Keywords

benzo[b]furans; C-C bond formation; cyclization; metal-free conditions; phase-transfer catalysts

Funding

  1. NSF [NS1-20872052, NSF-20090443]

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A variety of substituted benzo[b]furans are readily prepared in good to excellent yields under the mild reaction conditions from o-(1-alkynylphenoxy)-1-phenylethanone Under phase-transfer catalysis (PTC). This methodology accommodates simple experimental operations, inexpensive and environmentally benign catalysts, metal catalyst-free conditions, facile reagents and the possibility to conduct large-scale preparations. The development of carbon-carbon bond formation processes via an overall structural isomerization represents the most atom-economical approach.

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