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Synthesis 2007(6): 873-882  
DOI: 10.1055/s-2007-965939
PAPER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Lipophilic Benzo[b]furans from Cardanol

Roberta Berninia, Sandro Cacchi*b, Ilse De Salvea, Giancarlo Fabrizi*b
a Dipartimento A.B.A.C., Università degli Studi della Tuscia, Via S. Camillo De Lellis, 01100 Viterbo, Italy
b Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi ‘La Sapienza’, P. le A. Moro 5, 00185 Rome, Italy
Fax: +39(06)49912795; e-Mail: sandro.cacchi@uniroma1.it;
Further Information

Publication History

Received 29 November 2006
Publication Date:
20 February 2007 (online)

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Abstract

o-Iodocardanol, readily available from cardanol by iodination­, has been used to prepare a variety of lipophilic benzo[b]furans. 2-Substituted benzo[b]furans have been prepared by a Sonogashira cross-coupling/cyclization process. 2,3-Disubstituted benzo[b]furans have been obtained from o-alkynylcardanols by an oxypalladation/reductive elimination process.

Key words

cross-coupling - cyclization - alkynes - benzo[b]furans - catalysis

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