92722-14-0Relevant articles and documents
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.
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.
4-substituted tert-butyl phenylazocarboxylates-synthetic equivalents for the para-phenyl radical cation
Hoefling, Sarah B.,Bartuschat, Amelie L.,Heinrich, Markus R.
supporting information; experimental part, p. 9769 - 9772 (2011/02/22)
First electrophile, then radical: 4-Substituted tert-butyl phenylazocarboxylates 1 are versatile synthetic equivalents of the para-phenyl radical cation 2. The tert-butyloxycarbonylazo group enables nucleophilic substitutions to proceed under mild conditions and can later be employed for the generation of aryl radicals. Copyright
