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Issue 82, 2015
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Pd(ii)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans

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Abstract

A Pd(II)-catalyzed formal [4+1] cycloaddition of aryl diazoacetates and aryl propargyl alcohols is reported to afford 2,5-dihydrofuran derivatives as the dominant product over other traditional ones. The auto-tandem catalytic process is proposed to occur via Pd(II)-catalyzed intermolecular oxonium ylide formation and subsequent intramolecular trapping of the ylide with Pd(II)-activated alkynes.

Graphical abstract: Pd(ii)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans

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Supplementary files

Article information


Submitted
24 Jun 2015
Accepted
12 Aug 2015
First published
12 Aug 2015

Chem. Commun., 2015,51, 15204-15207
Article type
Communication
Author version available

Pd(II)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans

T. Shi, X. Guo, S. Teng and W. Hu, Chem. Commun., 2015, 51, 15204
DOI: 10.1039/C5CC05000F

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