Efficient syntheses of phosphonylated isochromenes by regioselective 6-endo-dig addition to carbon-carbon triple bond catalyzed by Pd(OAc)2

Fei Wang; Zhiwei Miao; Ruyu Chen

doi:10.1039/B908313H

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Efficient syntheses of phosphonylated isochromenes by regioselective 6-endo-dig addition to carbon-carbon triple bond catalyzed by Pd(OAc)₂†‡

Fei Wang,^a Zhiwei Miao*^ab and Ruyu Chen*^a

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* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, China
E-mail: miaozhiwei@nankai.edu.cn
Fax: +86 2350 2351
Tel: +86 2350 4783

^b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing, China

Abstract

Palladium(II)-catalyzed cycloisomerization of [(2-alkynylphenyl)hydroxymethyl]phosphonates 6 provides an efficient route to phosphonylated isochromenes 7 in THF at room temperature and the reaction proceeded in a regioselective manner leading to the 6-endo-dig products 7 in moderate to excellent yields.

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Supplementary files

Detailed description of experimental procedures, fullcharacterization of new compounds 7a-j shown in Table 2 PDF (2503K)

Article information

DOI: https://doi.org/10.1039/B908313H
Article type: Communication
Submitted: 27 Apr 2009
Accepted: 19 May 2009
First published: 28 May 2009

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Org. Biomol. Chem., 2009,7, 2848-2850

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Efficient syntheses of phosphonylated isochromenes by regioselective 6-endo-dig addition to carbon-carbon triple bond catalyzed by Pd(OAc)₂

F. Wang, Z. Miao and R. Chen, Org. Biomol. Chem., 2009, 7, 2848 DOI: 10.1039/B908313H

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Organic & Biomolecular Chemistry