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

被引：2

作者：

Park, Jong-Un ^{[1
]}

Huang, Liang-Zhu ^{[1
,2
]}

Cho, Ho-Jun ^{[1
]}

Park, Boyoung Y. ^{[3
]}

Kim, Ju Hyun ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Res Inst Nat Sci, Dept Chem BK21 Four, Jinju 52828, South Korea

[2] Yanan Univ, Coll Chem & Chem Engn, Yanan 716000, Shaanxi, Peoples R China

[3] Kyung Hee Univ, Coll Pharm, Seoul 02447, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

HIGHLY SUBSTITUTED PYRROLES; POLYSUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; STEP ECONOMY; THERMAL REARRANGEMENT; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; ATOM ECONOMY; COPPER;

D O I：

10.1021/acs.joc.2c02602

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：585 / 593

页数：9

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