Basicity-Controlled Reactivity of meta-OTf-Substituted Diaryliodonium Salts for Direct Arylation or Diels-Alder Cycloaddition of Pyrrole Derivatives

被引：3

作者：

Jiang, Ke ^{[1
,2
]}

Li, Xiaohui ^{[1
,2
]}

Wang, Limin ^{[1
,2
]}

Han, Jianwei ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Inst Fine Chem, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 13卷 / 09期

关键词：

Diaryliodonium salts; N-Heteroarenes; Direct arylation; Diels-Alder cycloaddition; Metal-free; N-ARYLATION; LATE-STAGE; C-H; ACCESS; CHEMISTRY;

D O I：

10.1002/ajoc.202400139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we explored the reactivity of meta-trifluoromethanesulfonate (OTf) substituted diaryliodonium salts under alkaline conditions. Two distinct pathways with direct arylation of pyrrole derivatives and Diels-Alder cycloaddition via aryne intermediates, have been found upon the relative alkalinity strength of potassium carbonates or hydroxides. This approach offers a straightforward and efficient route to synthesize heterocyclic aromatics under mild reaction conditions with tolerance of various functional groups.

引用

页数：5