Electrophotocatalytic diamination of vicinal C–H bonds

doi:10.1126/science.abf2798

GSTDTAP > 气候变化

DOI	10.1126/science.abf2798
	Electrophotocatalytic diamination of vicinal C–H bonds
	Tao Shen; Tristan H. Lambert
	2021-02-05
发表期刊	Science
出版年	2021
英文摘要	The conversion of C–H bonds into C–N bonds is broadly useful in producing pharmaceutically important compounds from simple, readily available feedstocks. Shen and Lambert report a method to induce this reaction twice in a row at benzylic and neighboring alkyl carbon centers, using acetonitrile solvent as a convenient source of nitrogen. The method relies on successive electrochemical and photochemical activation of a cyclopropenium catalyst and yields hydrogen gas as a clean co-product. Science , this issue p. [620][1] The conversion of unactivated carbon-hydrogen (C–H) bonds to carbon–nitrogen (C–N) bonds is a highly valued transformation. Existing strategies typically accomplish such reactions at only a single C–H site because the first derivatization diminishes the reactivity of surrounding C–H bonds. Here, we show that alkylated arenes can undergo vicinal C–H diamination reactions to form 1,2-diamine derivatives through an electrophotocatalytic strategy, using acetonitrile as both solvent and nitrogen source. The reaction is catalyzed by a trisaminocyclopropenium (TAC) ion, which undergoes anodic oxidation to furnish a stable radical dication while the cathodic reaction reduces protons to molecular hydrogen. Irradiation of the TAC radical dication (wavelength of maximum absorption of 450 to 550 nanometers) with a white-light compact fluorescent light generates a strongly oxidizing photoexcited intermediate. Depending on the electrolyte used, either 3,4-dihydroimidazole or aziridine products are obtained. [1]: /lookup/doi/10.1126/science.abf2798
领域	气候变化 ; 资源环境
URL	查看原文
引用统计
文献类型	期刊论文
条目标识符	http://119.78.100.173/C666/handle/2XK7JSWQ/314053
专题	气候变化资源环境科学
推荐引用方式 GB/T 7714	Tao Shen,Tristan H. Lambert. Electrophotocatalytic diamination of vicinal C–H bonds[J]. Science,2021.
APA	Tao Shen,&Tristan H. Lambert.(2021).Electrophotocatalytic diamination of vicinal C–H bonds.Science.
MLA	Tao Shen,et al."Electrophotocatalytic diamination of vicinal C–H bonds".Science (2021).