Photo‐induced sp3 C−H bond arylation, cyanation and nitroalkylation of tetrahydroisoquinolines (THIQs) under visible light irradiation using a combination of NHPI and Rose Bengal,Chemistry - An Asian Journal

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Photo‐induced sp3 C−H bond arylation, cyanation and nitroalkylation of tetrahydroisoquinolines (THIQs) under visible light irradiation using a combination of NHPI and Rose Bengal
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2020-10-13 , DOI: 10.1002/asia.202000999
Mahendra R. Patil ₁ , Jagrut Shah ₁ , A. Vijay Kumar ₁ , Anant R. Kapdi ₁

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This work reports a sustainable protocol for α‐arylation of tetrahydroisoquinolines (THIQs) with aryl diazonium salts using a combination of a cheap and stable oxidant, N‐hydroxyphthalimide (NHPI), and an inexpensive dye photosensitizer, Rose Bengal (RB), for the first time. The reaction was performed at ambient temperature using green LED light irradiation under an oxygen atmosphere. The developed α‐arylation protocol shows a diverse substrate scope for various THIQs and aryl diazonium salts. The work also explores nitroalkylation and cyanation under the developed reaction conditions. A possible SET mechanism is involved which was confirmed by ESI‐MS analysis of the reaction mixture.

中文翻译：

NHPI和玫瑰红的组合在可见光照射下，光诱导的四氢异喹啉（THIQs）的sp3 CH键芳基化，氰化和硝基烷基化

这项工作报告了一种廉价的稳定氧化剂N-羟基邻苯二甲酰亚胺（NHPI）和廉价的染料光敏剂玫瑰红（RB）结合使用的可持续方案，用于四氢异喹啉（THIQs）与芳基重氮盐的α芳基化反应。第一次。该反应在氧气气氛下使用绿色LED光照射在环境温度下进行。发达的α芳基化方案显示了各种THIQ和芳基重氮盐的底物范围广泛。这项工作还探索了在已开发的反应条件下的硝基烷基化和氰化。通过反应混合物的ESI-MS分析确认了可能的SET机理。

更新日期：2020-12-16

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