Visible-Light-Induced [2+2+1] Dearomative Cascade Cyclization of Indole/Furan Alkynes to Synthesize Sulfonyl Polycycles

被引：11

作者：

Luo, Jiajun ^{[1
]}

Zeng, Guohui ^{[1
]}

Cao, Xiaohui ^{[2
]}

Yin, Biaolin ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Peoples R China

[2] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 13期

基金：

中国国家自然科学基金;

关键词：

Polycycles; Photosynthesis; Cycloaddition; C-C bond formation; Synthetic methods; SULFUR-DIOXIDE; ACCESS; ENERGY; CYCLOADDITION; STATE;

D O I：

10.1002/adsc.202200331

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we report a visible-light-induced [2+2+1] dearomative cascade cyclization of indole/furan alkynes with NaHSO3, providing an array of diverse highly strained sulfonyl polycycles. Compared to our previous work, this method does not require the use of additional sacrificial oxidants and have wider reaction scope. Preliminary mechanistic studies suggest that the indole moiety initiated the reaction, which proceeded via single-electron oxidation pathway. An alkenyl radical formed by intramolecular addition capture SO2, and the resulting specie is cyclized to furnish the final product. Also, DFT calculations disclosed that the groups on the indole ring or at the side chain probably affect the single electron distribution at the reaction site of IM-RC-I, and the distribution may be a decisive factor of spirocyclization.

引用

页码：2197 / 2204

页数：8