1393841-64-9Relevant academic research and scientific papers
Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light
Li, Xipan,Liang, Kangjiang,Liu, Qian,Shen, Lei,Wei, Delian,Xia, Chengfeng,Zheng, Liyan
, p. 6996 - 7002 (2020/07/23)
The phenolate anion was discovered as a new photocatalyst with strong reduction potentials. Under visible light irradiation, the phenolate anion enabled the reduction of (hetero)aryl halides (including electron-rich aryl chlorides) to (hetero)aryl radicals through single electron transfer. Based on this new photocatalyst, a novel and efficient photocatalytic protocol for the intermolecular oxyarylation of olefins with aryl halides and TEMPOH was developed. The developed three-component coupling reaction proceeded under redox-neutral reaction conditions with stable and readily available synthons and exhibited broad substrate scope. The utility of this process was further highlighted by the diversified chemical manipulation of the resulting oxyarylation products and the late-stage modification of active pharmaceutical ingredients.
γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes
Zhu, Nengbo,Wang, Ting,Ge, Liang,Li, Yajun,Zhang, Xinhao,Bao, Hongli
supporting information, p. 4718 - 4721 (2017/09/23)
γ-Amino butyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Many GABA derivatives are used clinically to prevent or treat neurodegenerative diseases. Copper-catalyzed carboamination of alkenes offers an efficient method to fashion the core structure of GABA derivatives from alkenes. In this reaction, acetonitrile serves as the source of the carbon and nitrogen functionalities used to difunctionalize alkenes. Experimental and density functional theory (DFT) studies were carried out to investigate the mechanism of the reaction, and a copper-catalyzed radical-polar crossover mechanism is proposed.
Generation of Aryl Radicals through Reduction of Hypervalent Iodine(III) Compounds with TEMPONa: Radical Alkene Oxyarylation
Hartmann, Marcel,Li, Yi,Mück-Lichtenfeld, Christian,Studer, Armido
, p. 3485 - 3490 (2016/03/05)
A novel method for selective generation of aryl radicals from diaryliodonium salts and iodanylidene malonates with sodium 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPONa) as a single-electron transfer (SET) reducing reagent is described. In the presence of various alkenes, aryl radicals formed after SET-reduction of hypervalent iodine compounds undergo alkene addition and the adduct radicals that are thus generated are efficiently trapped by the concomitantly generated TEMPO radical to eventually afford oxyarylated products in moderate to very good yields. The efficiency of aryl radical generation of various iodine(III) reagents is studied and the generation of an iodanylidene malonate aryl radical is also investigated by computational methods.
Remazol-Catalyzed Hydroperoxyarylation of Styrenes
Chen, Ying-Ho,Lee, Ming,Lin, Yi-Zhen,Leow, Dasheng
supporting information, p. 1618 - 1621 (2015/08/06)
A mild photocatalytic hydroperoxyarylation of styrenes has been developed, in which a novel photocatalyst, remazol brilliant blue R (RBBR), is employed at low catalytic loading (1 mol%). The operationally easy procedure uses air as the dioxygen source. Simple mono-substituted styrenes react with aryl hydrazines in moderate-to-good yields. RBBR is proposed to act as a photosensitizer for the generation of singlet oxygen.
The photoredox-catalyzed meerwein addition reaction: Intermolecular amino-arylation of alkenes
Prasad Hari, Durga,Hering, Thea,K?nig, Burkhard
, p. 725 - 728 (2014/01/23)
A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of a 3-aryl-3,4- dihydroisoquinoline. From elimination to addition: A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of 3-aryl-3,4-dihydroisoquinoline. Copyright
Transition-metal-free oxyarylation of alkenes with aryl diazonium salts and TEMPONa
Hartmann, Marcel,Li, Yi,Studer, Armido
supporting information, p. 16516 - 16519,4 (2020/09/15)
The reaction of readily available TEMPONa with aryl diazonium salts allows for clean generation of the corresponding aryl radicals along with TEMPO. Aryl radical addition to alkenes with subsequent TEMPO trapping provides the corresponding oxyarylation pr
