56058-93-6Relevant academic research and scientific papers
Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions
Gingrich, Phillip W.,Olson, David E.,Tantillo, Dean J.,Tombari, Robert J.,Tuck, Jeremy R.,Yardeny, Noah
supporting information, p. 7575 - 7580 (2021/09/22)
Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.
Rh(III)-catalyzed [4?+?1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides toward 3-acyl-(2H)-indazoles
Zhu, Jiawei,Sun, Song,Cheng, Jiang
supporting information, p. 2284 - 2287 (2018/05/23)
A Rh(III)-catalyzed [4 + 1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides was developed to access 2H-indazoles in moderate to excellent yields with good functional group compatibilities. It proceeded with the sequential insertion of the Rh(III) carbene to the C?H bond and cyclization steps, where sulfoxonium ylides served as efficient and stable carbene precursor.
Palladium-catalyzed cascade oxidation/ sp 2 C-H acylation of azoarenes with aryl methanes
Xiong, Feng,Qian, Cheng,Lin, Dongen,Zeng, Wei,Lu, Xiaoxia
supporting information, p. 5444 - 5447 (2013/11/19)
A Pd-catalyzed cascade oxidation/sp2 C-H bond acylation of azoarenes was developed in which readily available aryl methanes were used as the in situ generated acyl sources. This reaction provides a convenient access to ortho-acyl azoarenes under mild conditions.
Palladium-catalyzed direct ortho alkoxylation of aromatic azo compounds with alcohols
Yin, Zhangwei,Jiang, Xiaoqing,Sun, Peipei
, p. 10002 - 10007 (2013/10/22)
An efficient and highly regioselective synthesis of 2-alkoxy aromatic azo compounds via palladium(II)-catalyzed alkoxylation of azobenzene derivatives directed by the azo group using alcohols as the alkoxylation reagents and PhI(OAc)2 as the ox
One step synthesis of azo compounds from nitroaromatics and anilines
Zhao, Rui,Tan, Chunyan,Xie, Yonghua,Gao, Chunmei,Liu, Hongxia,Jiang, Yuyang
supporting information; experimental part, p. 3805 - 3809 (2011/08/09)
A general and efficient method for synthesis of both symmetric and asymmetric aromatic azo compounds in one single step has been developed. The nitro compounds were reduced and the substituted anilines were oxidized by each other without any metal in the
Reactions of dry arenediazonium o-benzenedisulfonimides with triorganoindium compounds
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Giaveno, Cinzia
, p. 4884 - 4890 (2007/10/03)
The reaction between various arenediazonium o-benzenedisulfonimides and triorganoindium compounds is described. Depending on the reaction conditions, it is possible to obtain biaryls (16 examples, average yield of 79%) or diaryldiazenes (18 examples, average yield of 81 %). o-Benzenedisulfonimide can be recovered and reused to prepare additional arenediazonium o-benzenedisulfonimides. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
