40115-00-2Relevant academic research and scientific papers
Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source
Guo, Qi,Chen, Jingchao,Shen, Guoli,Lu, Guangfu,Yang, Xuemei,Tang, Yan,Zhu, Yuanbin,Wu, Shiyuan,Fan, Baomin
, p. 540 - 546 (2021/12/27)
A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.
Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N -Centered Radicals in an Electrochemical C(sp3)-H Arylation Reaction
Alhumade, Hesham,Gao, Renfei,Huang, Cunlong,Lei, Aiwen,Liu, Yichang,Liu, Zhao,Qi, Xiaotian,Shi, Biyin,Wang, Shengchun
supporting information, p. 20863 - 20872 (2021/12/14)
Electrochemical synthesis has been rapidly developed over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electroche
Photo-Induced Cross-Dehydrogenative Alkylation of Heteroarenes with Alkanes under Aerobic Conditions
Xu, Jun,Cai, Heng,Shen, Jiabin,Shen, Chao,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 17816 - 17832 (2021/12/17)
We report a Minisci-type cross-dehydrogenative alkylation in an aerobic atmosphere using abundant and inexpensive cerium chloride as a photocatalyst and air as an oxidant. This photoreaction exhibits excellent tolerance to functional groups and is suitabl
Design and implementation of a catalytic electron donor?acceptor complex platform for radical trifluoromethylation and alkylation
Stephenson, Corey R.J.,McClain, Edward J.,Monos, Timothy M.,Mori, Mayuko,Beatty, Joel W.
, p. 12636 - 12641 (2020/11/18)
Electron donor?acceptor (EDA) complexes can controllably generate radicals under mild conditions through selective photoexcitation events. However, unproductive reactivity from fast deactivation of the photoexcited complexes through back electron transfer has slowed the development of EDA complexes in synthetic methodology. Here, we disclose the study of EDA complexes derived from 2-methoxynaphthalene donor and acylated ethyl isonicotinate N-oxide acceptor that undergo a fast N?O bond fragmentation event upon photoexcitation. This reaction design not only overcomes the limitations of back electron transfer but also enables regeneration of the donor species, representing a rare example of EDA photochemistry in a catalytic regime. The synthetic utility is demonstrated through visible light-driven radical trifluoromethylation and Minisci alkylation reactions. The scalability of the EDA complex-promoted reaction is evidenced by the successful multigram-scale trifluoromethylation of methyl N-Boc pyrrole-2-carboxylate in a continuous flow manifold.
Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
Che, Tong,Kang, Hua-Jie,Peng, Dongming,Shu, Bing,Song, Jia-Lin,Wang, Xiao-Tong,Xie, Hui,Zhang, Luyong,Zhang, Shang-Shi,Zhong, Mei
supporting information, (2020/06/25)
A synthetic method for quinoxaline derivatives from the [4+2] annulation of β-keto sulfoxonium ylides and o-phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional-group compatibility. Moreover, this cyclization strategy was successfully applied in late-stage modification for structurally complex bioactive compounds.
Cross-Dehydrogenative Coupling of Strong C(sp3)-H with N-Heteroarenes through Visible-Light-Induced Energy Transfer
An, Guanghui,Li, Guangming,Tian, Chao,Tian, Haitao,Yang, Hui
supporting information, p. 7709 - 7715 (2020/10/09)
The sustainable cross-dehydrogenative coupling of strong C(sp3)-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive
Visible Light-Promoted Aliphatic C-H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent
Zhao, Hong,Jin, Jian
supporting information, p. 6179 - 6184 (2019/09/06)
A mild, practical method for direct arylation of unactivated C(sp3)-H bonds with heteroarenes has been achieved via photochemistry. Selectfluor is used as a hydrogen atom transfer reagent under visible light irradiation. A diverse range of chem
Organocatalyzed, Visible-Light Photoredox-Mediated, One-Pot Minisci Reaction Using Carboxylic Acids via N-(Acyloxy)phthalimides
Sherwood, Trevor C.,Li, Ning,Yazdani, Aliza N.,Dhar, T. G. Murali
, p. 3000 - 3012 (2018/03/09)
An improved, one-pot Minisci reaction has been developed using visible light, an organic photocatalyst, and carboxylic acids as radical precursors via the intermediacy of in situ-generated N-(acyloxy)phthalimides. The conditions employed are mild, demonstrate a high degree of functional group tolerance, and do not require a large excess of the carboxylic acid reactant. As a result, this reaction can be applied to drug-like scaffolds and molecules with sensitive functional groups, enabling late-stage functionalization, which is of high interest to medicinal chemistry.
Versatile cross-dehydrogenative coupling of heteroaromatics and hydrogen donors via decatungstate photocatalysis
Quattrini, Matteo C.,Fujii, Saki,Yamada, Keiichi,Fukuyama, Takahide,Ravelli, Davide,Fagnoni, Maurizio,Ryu, Ilhyong
supporting information, p. 2335 - 2338 (2017/02/23)
A facile sunlight-induced derivatization of heteroaromatics via photocatalyzed C-H functionalization in amides, ethers, alkanes and aldehydes is described. Tetrabutylammonium decatungstate (TBADT) was used as the photocatalyst and allowed to carry out the
Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
Galloway, Jordan D.,Mai, Duy N.,Baxter, Ryan D.
supporting information, p. 5772 - 5775 (2017/11/10)
A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.
