Visible-Light-Mediated Synthesis of Cyclobutene-Fused Indolizidines and Related Structural Analogs

被引：72

作者：

Zhu, Min ^{[1
,2
]}

Huang, Xu-Lun ^{[1
,2
]}

Xu, Hao ^{[1
,2
]}

Zhang, Xiao ^{[1
]}

Zheng, Chao ^{[1
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem,Ctr Excellence Mol Synth, Shanghai 200032, Peoples R China

[2] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China

来源：

CCS CHEMISTRY | 2021年 / 3卷 / 01期

关键词：

cyclobutene; dearomatization; energy transfer; indole; indolizidine; PHOTOCHEMICAL CYCLOADDITION REACTIONS; DIMETHYL ACETYLENEDICARBOXYLATE; N-BENZOYLINDOLE; PHOTOCYCLOADDITION; ALKALOIDS; PHOTOCATALYSIS; DEAROMATIZATION; PYRROLIZIDINES; REARRANGEMENT; CYCLIZATION;

D O I：

10.31635/ccschem.020.202000254

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Expedient assembly of unprecedented molecular scaffolds from readily accessible starting materials in a sustainable fashion is highly pursued in modern organic chemistry. Herein, the first catalytic intramolecular dearomative [2 + 2] cycloaddition of indoles or pyrroles with alkynes is achieved via visible-lightmediated energy-transfer catalysis. This method enables the synthesis of cyclobutene-fused indolizidines, which are otherwise challenging to access, in high yields with exclusive selectivity. The reaction profiles are well documented by density functional theory (DFT) calculations. In addition, this protocol can be extended to the synthesis of cyclobutane-fused indolizidines and related structural analogs. Diverse elaborations of the products are achieved.

引用

页码：652 / 664

页数：13

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