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
收藏
页码：585 / 593
页数：9
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