Dehydrogenative Photocyclization of 3-Styryl Indoles to Fused Indole Systems

被引：0

作者：

Taskesenligil, Yunus ^{[1
]}

Saracoglu, Nurullah ^{[1
,2
]}

机构：

[1] Atatuurk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkiye

[2] Ankara Univ, Biotechnol Inst, TR-06135 Ankara, Turkiye

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

关键词：

ANNULATION; CYCLIZATION; DERIVATIVES; CARBAZOLES;

D O I：

10.1021/acs.joc.4c02103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 5-aryl- or 5,6-diaryl-11H-benzo[a]carbazoles has been achieved from 3-styryl indoles through catalyst-free photoinitiated dehydrogenative cyclization transformation, providing a range of structurally diverse products in excellent yields under mild conditions. The protocol is also applicable to furan and thiophene samples. This Mallory-type reaction takes place in an argon atmosphere without external oxidants. Finally, detailed mechanistic studies were performed, and kinetic isotope effect experiments indicate that dehydrogenative annulation reaction involves photoinduced 6 pi-electrocyclic ring-closing and hydrogen evolution cascade processes.

引用

页码：17447 / 17452

页数：6

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