One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3 -Triazoles and 2-Hydroxymethylallyl Carbonates
  • Park, J.-U.
  • Huang, L.-Z.
  • Cho, H.-J.
  • Park, B.Y.
  • Kim, J.H.
Citations

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초록

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 NH pyrroles with high efficiency. © 2022 American Chemical Society.

키워드

HIGHLY SUBSTITUTED PYRROLESPOLYSUBSTITUTED PYRROLESREGIOSELECTIVE SYNTHESISTERMINAL ALKYNESSTEP ECONOMYTHERMAL REARRANGEMENTEFFICIENT SYNTHESISORGANIC-SYNTHESISATOM ECONOMYCOPPER
제목
One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3 -Triazoles and 2-Hydroxymethylallyl Carbonates
저자
Park, J.-U.Huang, L.-Z.Cho, H.-J.Park, B.Y.Kim, J.H.
DOI
10.1021/acs.joc.2c02602
발행일
2023-01
유형
Article
저널명
Journal of Organic Chemistry
88
1
페이지
585 ~ 593