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Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N,N′‐Dimethylpropylene Urea as H‐Donor
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-01-29 , DOI: 10.1002/adsc.201700937
Sai-Hu Cai 1, 2 , Ding-Xing Wang 1 , Lu Ye 1 , Ze-Yao Liu 1 , Chao Feng 1 , Teck-Peng Loh 2, 3
Affiliation  

Synthesis of 3,4‐pyrroline derivatives via visible‐light‐induced hydro/oxyimination of unactivated olefins is reported. In the presence of the photoredox catalyst fac‐Ir(ppy)3, the key iminyl radical intermediate can be readily generated from O‐acyl oximes, and undergoes intramolecular cyclization and H‐abstraction from solvent or is trapped by TEMPO to give the corresponding hydro/oxyimination product, respectively. Mechanistic investigations indicate that N,N′‐dimethylpropylene urea (DMPU) works as both reducing agent for catalyst regeneration and H‐donor for product formation in this process.

中文翻译:

以N,N'-二甲基丙烯脲为H-供体的可见光促进未活化烯烃的加氢氢化合成吡咯啉

据报道,通过可见光诱导的未活化烯烃的加氢/氧合反应合成了3,4-吡咯啉衍生物。在存在光氧化还原催化剂fac- Ir(ppy)3的情况下,关键的亚胺基自由基中间体很容易从O-酰基肟中生成,并经历分子内环化和溶剂中H的吸收或被TEMPO捕集,得到相应的加氢化合物。 /氧合产物。机理研究表明,在此过程中,N,N'-二甲基丙烯脲(DMPU)既可作为催化剂再生的还原剂,又可作为产物形成的H-供体。
更新日期:2018-01-29
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