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Issue 40, 2018
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Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones

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Abstract

A palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones is reported. The alkylpalladium intermediate coupled with the diazo compound, generating the second alkylpalladium species bearing two β-H, which generated a terminal alkene as the major products in the anti-Zaitsev way via the highly regioselective β-H elimination. It provided a new way to synthesize tetrahydropyridine derivatives bearing a terminal alkene.

Graphical abstract: Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones

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Publication details

The article was received on 28 Jul 2018, accepted on 24 Sep 2018 and first published on 25 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB01821A
Citation: Org. Biomol. Chem., 2018,16, 7356-7360
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    Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones

    J. Li, X. Chi, L. Meng, L. Jiao, W. Shang, P. Wang, D. Zhang, Y. Dong, Q. Liu and H. Liu, Org. Biomol. Chem., 2018, 16, 7356
    DOI: 10.1039/C8OB01821A

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