Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives.

Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives.
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DOI:
10.1021/acs.orglett.3c02292
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发表时间:
2023-09-08
期刊:
影响因子:
5.2
通讯作者:
Parasram, Marvin
Parasram, Marvin
中科院分区:
化学1区
文献类型:
--
作者:
Mitchell, Joshua K.;Hussain, Waseem A.;Bansode, Ajay H.;O'Connor, Ryan M.;Wise, Dan E.;Choe, Michael H.;Parasram, Marvin

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在这里,我们报告了一种由光激发的硝基芳烃促进的醇、胺、醛和亚胺的厌氧氧化反应。机理研究支持这样的观点,即光激发的硝基芳烃与醇和胺经历双氢原子转移(HAT)步骤,以提供相应的酮和亚胺产物。在醛和亚胺存在下,连续的HAT和氧原子转移(OAT)事件分别产生羧酸和酰胺。这种转变适用于连续光流装置,从而缩短了反应时间。
Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support the idea that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide the respective ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom transfer (OAT) events occur to yield carboxylic acids and amides, respectively. This transformation is amenable to a continuous-photoflow setup, which led to reduced reaction times.
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