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Synlett 2002(1): 0065-0068
DOI: 10.1055/s-2002-19352
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of 2,3-Dihydrofurans via the Highly Selective Pd(0)-Catalyzed Coupling-Cyclization Reaction of 3,4-Allenols with Aryl Iodides

Shengming Ma*, Wenzhong Gao
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: masm@pub.sioc.ac.cn;
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Publication History

Received 25 September 2001
Publication Date:
01 February 2007 (online)

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Abstract

Highly selective coupling-cyclization of 3,4-allenols with aryl iodides via the oxidative addition-exo-mode oxypalladation-reductive elimination sequence afforded 2,3-dihydrofurans efficiently. The cyclization mode and the regioselectivity observed for 3,4-allenols are unique and different from what was reported previously.

Key words

alcohols - allenes - furans - palladium - cyclizations