Issue 17, 2022

The regioselective annulation of N-methylpyridinium ylides with alkenes enabled by palladium catalysis: access to 3-unsubstituted indolizine derivatives

Abstract

The first catalytic protocol for the regioselective [3 + 2] annulation of N-methyl pyridinium ylides with alkenes to establish various valuable 3-unsubstituted indolizine derivatives is accomplished via palladium catalysis at the unactivated position. The reaction supports a wide range of substrates and shows excellent functional group tolerance, delivering the corresponding annulation products in good to excellent yields. In particular, the gram-scale preparation and valuable diversified derivatization of annulation products further illustrate the potential of this catalytic system. Furthermore, combined computational and experimental studies corroborate the proposed reaction mechanism.

Graphical abstract: The regioselective annulation of N-methylpyridinium ylides with alkenes enabled by palladium catalysis: access to 3-unsubstituted indolizine derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
05 Apr 2022
Accepted
10 Jul 2022
First published
12 Jul 2022

Org. Chem. Front., 2022,9, 4719-4725

The regioselective annulation of N-methylpyridinium ylides with alkenes enabled by palladium catalysis: access to 3-unsubstituted indolizine derivatives

Q. Gou, Q. Zhu, M. Deng, W. Li, X. Ran, J. Xie, H. Huang, X. Tan and M. Zhu, Org. Chem. Front., 2022, 9, 4719 DOI: 10.1039/D2QO00555G

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