966-88-1Relevant articles and documents
Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate
Tan, Zheng,Zhang, Shiwei,Zhang, Yan,Li, Yunpeng,Ni, Minjie,Feng, Bainian
, p. 9384 - 9399 (2017/09/23)
A metal-free and cost-effective synthetic protocol for the trifluoromethylation of N,N-disubstituted hydrazones with Langlois's reagent (CF3SO2Na) to afford the corresponding functionalized trifluoromethyl ketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a trifluoroalkyl radical may be involved in the reaction. Applications of the methodology in industry will be found and the development of new methods for trifluoromethylation with Langlois's reagent will be continued in our laboratory.
A Single Electron Transfer (SET) Approach to C-H Amidation of Hydrazones via Visible-Light Photoredox Catalysis
Zhang, Muliang,Duan, Yingqian,Li, Weipeng,Xu, Pan,Cheng, Jian,Yu, Shouyun,Zhu, Chengjian
supporting information, p. 5356 - 5359 (2016/11/02)
The reductive single electron transfer (SET) umpolung amination of aldehyde-derived hydrazones has been developed through visible-light-promoted photoredox catalysis. The ideal transformation of hydrazones into the corresponding hydrazonamide through selective carbon-hydrogen (C-H) bond functionalization represents one of the most step- and atom-economical methods. This SET umpolung strategy features mild conditions and a remarkably broad substrate scope, offering an entirely new substrate class to direct C-H amination.
An expedient approach to enhance Mizoroki-Heck coupling reaction by infrared irradiation using palladacycle compounds
Ortega-Jimnez, Fernando,Domnguez-Villa, Francisco X.,Rosas-Snchez, Alfredo,Penieres-Carrillo, Guillermo,Lpez-Corts, Jos G.,Ortega-Alfaro, M. Carmen
, p. 556 - 560 (2015/08/04)
An alternative and environmentally friendly strategy to promote the Mizoroki-Heck cross-coupling reaction by the use of infrared irradiation using palladacycles as precatalysts is reported. Coupling products are obtained in high yield and short reaction time. A comparison with the classical use of reflux conditions, and commercial sources of palladium complexes, shows the advantages of this new alternative for promoting coupling reactions.
Fast hydrazone reactants: Electronic and acid/base effects strongly influence rate at biological pH
Kool, Eric T.,Park, Do-Hyoung,Crisalli, Pete
supporting information, p. 17663 - 17666 (2014/01/06)
Kinetics studies with structurally varied aldehydes and ketones in aqueous buffer at pH 7.4 reveal that carbonyl compounds with neighboring acid/base groups form hydrazones at accelerated rates. Similarly, tests of a hydrazine with a neighboring carboxylic acid group show that it also reacts at an accelerated rate. Rate constants for the fastest carbonyl/hydrazine combinations are 2-20 M-1 s-1, which is faster than recent strain-promoted cycloaddition reactions.
Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
, p. 11232 - 11256 (2013/02/23)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
METAL-ASSISTED REACTIONS-PART 11 RAPID REDUCTION OF N-NITROSOAMINES TO N,N-DISUBSTITUTED HYDRAZINES; THE UTILITY OF SOME LOW-VALENT TITANIUM REAGENTS
Entwistle, Ian D.,Johnstone, A. W.,Wilby, Anna H.
, p. 419 - 423 (2007/10/02)
The rapid reduction of N-nitrosoamines to N,N-disubstituted hydrazines by a low-valent titanium reagent is described.The reagent is selective in that many other functional groups are unaffected by it.The nature of the low-valent titanium reagent is discussed in terms of experimental results of comparisons of its reactivity and that of other low-valent titanium reducing agents.