92491-22-0Relevant academic research and scientific papers
Encapsulation of Porphyrin-Fe/Cu Complexes into Coordination Space for Enhanced Selective Oxidative Dehydrogenation of Aromatic Hydrazides
Zhang, Dongxu,Du, Peiyao,Liu, Jia,Zhang, Ruizhong,Zhang, Zhen,Han, Zhengang,Chen, Jing,Lu, Xiaoquan
, (2020)
The encapsulation of specific nanoentities into hollow nanomaterials derived from metal organic frameworks has attracted continuous and growing research attentions owing to their unique structural properties and unusual synergistic functions. Herein, usin
Hydrogen peroxide based oxidation of hydrazines using HBr catalyst
Du, Wanting,Ma, Zichao,Shao, Liming,Wang, Jian
, (2021/11/18)
Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.
Electrochemical dehydrogenation of hydrazines to azo compounds
Du, Ke-Si,Huang, Jing-Mei
, p. 1680 - 1685 (2019/04/08)
A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.
Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP
Kim, Min Hye,Kim, Jinho
, p. 1673 - 1679 (2018/02/09)
Recently, various fruitful organic reactions such as a catalytic Mitsunobu reaction were reported by virtue of alkyl 2-phenylazocarboxylates, however, the synthesis of alkyl 2-phenylazocarboxylates largely depended on the stoichiometric use of toxic oxidants. In this manuscript, an environment-friendly aerobic oxidative transformation of alkyl 2-phenylhydrazinecarboxylates to alkyl 2-phenylazocarboxylates is disclosed. The use of CuCl and DMAP system efficiently catalyzed the aerobic oxidation of alkyl 2-phenylhydrazinecarboxylates under mild conditions. The reaction rate of the present Cu-catalysis was much faster than that of the previously reported Fe-catalysis, and a variety of azo products were synthesized within 3 h. The present protocol was effective on larger scale. It was observed that the produced azo compound could undergo various reactions without isolation through one-pot sequential protocols.
Synthesis of Hydrazines via Radical Generation and Addition of Azocarboxylic tert -Butyl Esters
Ru, Chen-Hao,Guo, Shi-Huan,Pan, Gao-Fei,Zhu, Xue-Qing,Gao, Ya-Ru,Wang, Yong-Qiang
supporting information, p. 1910 - 1913 (2018/04/16)
A new chemistry of azo compounds that is a radical generation and addition in situ of azocarboxylic tert-butyl esters to synthesize hydrazines has been described. The protocol provides a novel strategy for the synthesis of various hydrazines. The advantag
Synthesis of Indazolones via Friedel-Crafts Cyclization of Blocked (Masked) N-Isocyanates
Elkaeed, Eslam B.,An, Jing,Beauchemin, André M.
, p. 9890 - 9897 (2017/09/23)
Nitrogen-substituted isocyanates (N-isocyanates) are rare amphoteric reagents with high, but underdeveloped synthetic potential. Herein, we study the formation of indazolones by Friedel-Crafts cyclization of N-isocyanates using blocked (masked) N-isocyanate precursors: the effect of the masking group and the reaction scope have been delineated. Substrate synthesis has also been improved using a reported copper-catalyzed coupling of arylbismuth(V) reagents that is compatible with the hemilabile OPh blocking group.
Cp?Rh(III)-catalyzed electrophilic amination of arylboronic acids with azo compounds for synthesis of arylhydrazides
Lau, Yan-Fung,Chan, Chun-Ming,Zhou, Zhongyuan,Yu, Wing-Yiu
supporting information, p. 6821 - 6825 (2016/07/21)
A [Cp?Rh(iii)]-catalyzed electrophilic amination of arylboronic acids with diethyl azodicarboxylate (DEAD) was developed, and arylhydrazides were produced in excellent yields and selectivity. The analogous amination with the arylazocarboxylates afforded t
Cu(II)-catalyzed cross-dehydrogenative coupling reaction of: N ′-acyl arylhydrazines and phosphites
Zhang, Ji-Quan,Xiong, Yan-Shi,Chan, Albert S. C.,Lu, Gui
, p. 84587 - 84591 (2016/10/12)
A novel Cu(ii)-catalyzed cross-dehydrogenative coupling reaction of N′-aryl acylhydrazines and dialkyl phosphites has been developed for the synthesis of phosphorylhydrazides by using NMO as an external oxidant and AgNO3 as additive. Various N′
Catalytic Aerobic Oxidation of Arylhydrazides with Iron Phthalocyanine
Hashimoto, Takuma,Hirose, Daisuke,Taniguchi, Tsuyoshi
supporting information, p. 3346 - 3352 (2015/11/03)
A convenient method for the synthesis of 2-arylazocarboxylates from 2-arylhydrazinecarboxylates by aerobic oxidation with iron phthalocyanine is described. The reaction is applicable to oxidative activation of 1-acyl-2-phenylhydrazines. Some preliminary experiments suggest Michaelis-Menten kinetics and participation of radical species in the reaction mechanism.
Rhodium(III)-catalyzed cyclative capture approach to diverse 1-aminoindoline derivatives at room temperature
Zhao, Dongbing,Vsquez-Cspedes, Suhelen,Glorius, Frank
supporting information, p. 1657 - 1661 (2015/01/30)
A RhIII-catalyzed C-H activation/cyclative capture approach, involving a nucleophilic addition of C(sp3)-Rh species to polarized double bonds is reported. This constitutes the first intermolecular catalytic method to directly access 1-aminoindolines with a broad substituent scope under mild conditions.
