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

Jong-Un ParkLiang-Zhu HuangHo-Jun ChoBoyoung Y ParkJu Hyun Kim
Published in: The Journal of organic chemistry (2022)
An efficient, tandem one-pot approach to synthesize multisubstituted 2-acylpyrroles from readily prepared N -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 N H pyrroles with high efficiency.
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