One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3Triazoles and 2-Hydroxymethylallyl Carbonates.

J Org Chem

Department of Chemistry (BK21 Four), Research Institute of Natural Science, Gyeongsang National University, Jinju 52828, Korea.

Published: January 2023

An efficient, tandem one-pot approach to synthesize multisubstituted 2-acylpyrroles from readily prepared -tosyl triazoles and 2-hydroxymethylallyl carbonates is reported. The reaction proceeds via Rh(II)-catalyzed O-H insertion, [3,3]-sigmatropic rearrangement, Pd(0)-catalyzed oxidative addition, intramolecular cyclization, DBU-promoted E1cB elimination, double bond isomerization, and aromatization, enabling the disconnection and formation of multiple bonds in one reactor. The approach represents a highly regioselective way to access di-, tri-, and tetra-substituted H pyrroles with high efficiency.

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http://dx.doi.org/10.1021/acs.joc.2c02602DOI Listing

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