1601-18-9Relevant articles and documents
Organoiridium catalyzed hydrogen isotope exchange: Ligand effects on catalyst activity and regioselectivity
Shu,Chen,Heys
, p. 87 - 93 (1996)
Several iridium complexes [Ircod)L2]X (L = phosphine ligand) were used as precatalysts for the exchange labeling of a range of model compounds with deuterium gas. Complexes with monodentate L (e.g. PMePh2, PPh3 and substituted derivatives thereof) catalyzed exchange selectively of hydrogens four bonds away from a coordinative heteroatom in the substrate, while those with bidentate L (bis(diphenylphosphino)ethane (dppe) and bis(diphenylphosphino)butane) catalyzed exchange of hydrogens both four and five bonds away from a coordinative heteroatom. At heavier loadings, some monodentate complexes also catalyzed five-bond labeling of some substrates. [Ir(cod)(dppe)]BF4 catalyzed the tritium labeling of methyl 6-methoxynaphth-2-ylacetate at C1 and C3.
Photolysis of indomethacin in methanol
Wu, An-Bang,Cheng, Hui-Wen,Hu, Chien-Ming,Chen, Fu-An,Chou, Tzu-Chang,Chen, Chau-Yang
, p. 621 - 622 (1997)
A novel photo-oxidation product containing a six-membered 1,2-dioxane ring was isolated from the photolysis of indomethacin in methanol and a possible mechanism is proposed.
Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis
Chiba, Shunsuke,Li, Haoyu,Liu, Yuliang
supporting information, p. 6264 - 6267 (2021/07/02)
A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.
Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information, p. 2713 - 2718 (2021/06/25)
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations
Svec, Riley L.,Hergenrother, Paul J.
supporting information, p. 1857 - 1862 (2019/12/27)
Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.