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Photocatalytic Thio/Selenosulfonylation–Bicyclization of Indole-Tethered 1,6-Enynes Leading to Substituted Benzo[c]pyrrolo[1,2,3-lm]carbazoles
Organic Letters ( IF 5.2 ) Pub Date : 2024-04-29 , DOI: 10.1021/acs.orglett.4c00981
Hang-Dong Zuo 1, 2 , Xi Chen 1, 3 , Yue Zhang 1, 3 , Jian-Wu Liu 1, 3 , Sheng-Hu Yan 1, 3 , Guigen Li 4 , Jia-Yin Wang 1, 3
Affiliation  

The photocatalyzed radical-triggered thio/selenosulfonylation–bicyclization of indole-tethered 1,6-enynes has been established for the first time, enabling the synthesis of various previously unreported thio/selenosulfonylated benzo[c]pyrrolo[1,2,3-lm]carbazoles with moderate to good yields under mild conditions. The reaction pathway was proposed, consisting of energy transfer, homolytic cleavage, radical addition, 5-exo-dig, radical coupling, and a Mallory reaction cascade. This approach exhibits a wide substrate compatibility and excellent tolerability toward various functional groups and is characterized by its remarkable efficiency in both bond formation and annulation.

中文翻译:

光催化硫代/硒磺酰化-吲哚束缚的1,6-烯炔的双环化产生取代的苯并[c]吡咯并[1,2,3-lm]咔唑

首次建立了光催化自由基引发的吲哚束缚的1,6-烯炔的硫代/硒磺酰化-双环化,从而能够合成各种以前未报道的硫代/硒磺酰化苯并[ c ]吡咯并[1,2,3- lm] ]咔唑在温和条件下具有中等至良好的产率。提出了反应途径,包括能量转移、均裂、自由基加成、5- exo - dig、自由基偶联和马洛里反应级联。该方法表现出广泛的底物兼容性和对各种官能团的优异耐受性,其特点是在成键和成环方面具有显着的效率。
更新日期:2024-04-29
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