Rh(III)-catalyzed C6-selective Acylmethylation and Carboxymethylation of 2-Pyridones with Diazo Compounds

被引：6

作者：

Wang, Xinyu ^{[1
]}

He, Zhongyu ^{[1
]}

Xu, Xin ^{[1
]}

Zhao, Haoqiang ^{[1
]}

Pan, Yixiao ^{[1
]}

Li, Huanrong ^{[1
]}

Xu, Lijin ^{[1
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

来源：

CHEMCATCHEM | 2021年 / 13卷 / 07期

基金：

中国国家自然科学基金;

关键词：

2-pyridone; acylmethylation; carboxymethylation; rhodium; diazo compound; C-H ACTIVATION; C3-SELECTIVE DIRECT ALKYLATION; N-OXIDES; RHODIUM(III)-CATALYZED SYNTHESIS; CARBENOID FUNCTIONALIZATION; DIRECT OLEFINATION; ARYLATION; PYRIDONES; BOND; HETEROCYCLES;

D O I：

10.1002/cctc.202002016

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Chelation-assisted C6-selective acylmethylation and carboxymethylation of 2-pyridones with diazo carbonyl compounds under [Cp*RhCl2](2)/AgSbF6 catalysis have been developed. Deesterificative C6-acylmethylation of 2-pyridones with diazo tert-butyl ester compounds proceeds effectively with the use of HOAc additive and hexafluoroisopropanol (HFIP) solvent, whereas switching to NaOAc additive and MeOH solvent enables efficient deacylative C6-carboxymethylation of 2-pyridones with alkyl 2-diazo-3-oxobutanoates. The procedures are characterized by excellent regioselectivity, high efficiency, broad substrate scope, wide functional group compatibility and gram-scalability. Preliminary mechanistic experiments are conducted to gain insights into the reaction mechanisms.

引用

页码：1730 / 1737

页数：8

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