Balancing Activity and Stability in Halogen-Bonding Catalysis: Iodopyridinium-Catalyzed One-Pot Synthesis of 2,3-Dihydropyridinones

被引：7

作者：

Li, Yi ^{[1
]}

Ge, Yicen ^{[1
]}

Sun, Rui ^{[2
]}

Yang, Xiao ^{[2
]}

Huang, Shipeng ^{[1
]}

Dong, Huajian ^{[1
]}

Liu, Yunyao ^{[1
]}

Xue, Haodan ^{[1
]}

Ma, Xiaoyan ^{[1
]}

Fu, Haiyan ^{[3
]}

Chen, Zeqin ^{[1
]}

机构：

[1] Chengdu Univ Technol, Coll Mat Chem & Chem Engn, Chengdu 610059, Sichuan, Peoples R China

[2] Chongqing Univ Technol, Sch Chem & Chem Engn, Chongqing 400054, Peoples R China

[3] Sichuan Univ, Minist Educ, Key Lab Green Chem & Technol, Coll Chem, Chengdu 610064, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; DANISHEFSKYS DIENE; ORGANIC-SYNTHESIS; DONOR CATALYST; LEWIS-ACID; ACTIVATION; ALDEHYDES; HYDROGEN; SALT; DERIVATIVES;

D O I：

10.1021/acs.joc.3c01028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot cascade reaction for 2,3-dihydropyridinonesynthesiswas accomplished with 3-fluoro-2-iodo-1-methylpyridinium triflateas the halogen bond catalyst. The desired [4+2] cycloaddition products,bearing aryl, heteroaryl, alkyl, and alicyclic substituents, weresuccessfully furnished in 28-99% yields. Mechanistic investigationsproved that a strong halogen-bonding interaction forged between theiodopyridinium catalyst and imine intermediate was essential to dynamicallymasking the vulnerable C-I bond on the catalyst and acceleratingthe following aza-Diels-Alder reaction.

引用

页码：11069 / 11082

页数：14

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