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
收藏
页码：1730 / 1737
页数：8
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