Issue 28, 2015

Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols

Abstract

Palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols produces polysubstituted indoles or benzothiophenes, respectively. The reaction proceeds through 2-furylmethylene palladium iodide intermediates, which undergo furan ring opening followed by ring closure to form indoles or benzothiophenes. This reaction will expand the synthetic applications of furfural derivatives.

Graphical abstract: Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2015
Accepted
24 Feb 2015
First published
25 Feb 2015

Chem. Commun., 2015,51, 6126-6129

Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols

B. Yin, X. Zhang, X. Zhang, H. Peng, W. Zhou, B. Liu and H. Jiang, Chem. Commun., 2015, 51, 6126 DOI: 10.1039/C5CC00267B

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