Issue 19, 2024

Tandem site-selective bromination and highly regioselective Heck reaction of N-allyl enaminones: chemodivergent synthesis of polysubstituted pyrroles and pyridines

Abstract

The Heck reaction is an efficient strategy for constructing C–C bonds, but a one-pot bromination followed by a Heck reaction of N-allyl enaminones has remained completely unexplored. In this paper, we present the first example of a cascade transient halogenation and Heck reaction of N-allyl enaminones for the direct formation of pyrrole and pyridine heterocycles by simply varying the substituents of N-allyl enaminones. This method not only overcomes the limitations of previously known Heck reactions, such as the requirement for the pre-installation of a halogen atom at a desired position, but also addresses the issue of regioselectivity in Heck reactions with N-allyl enaminones as substrates. The ready availability of materials, inexpensive reagents, and excellent functional group compatibility make this method a valuable synthetic tool for constructing polysubstituted pyrroles and pyridine scaffolds, thereby enhancing the potential of this protocol for applications in the pharmaceutical industry.

Graphical abstract: Tandem site-selective bromination and highly regioselective Heck reaction of N-allyl enaminones: chemodivergent synthesis of polysubstituted pyrroles and pyridines

Supplementary files

Article information

Article type
Research Article
Submitted
25 Jun 2024
Accepted
12 Aug 2024
First published
14 Aug 2024

Org. Chem. Front., 2024,11, 5532-5537

Tandem site-selective bromination and highly regioselective Heck reaction of N-allyl enaminones: chemodivergent synthesis of polysubstituted pyrroles and pyridines

X. Duan, J. Wang, H. Li, F. Du, R. Chen, W. Lian and M. Shi, Org. Chem. Front., 2024, 11, 5532 DOI: 10.1039/D4QO01168F

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