7541-20-0Relevant academic research and scientific papers
Copper porphyrin-catalyzed C(sp2)—O bond construction via coupling phenols with formamides
Yang, Shuang,Chen, Xiao-Yan,Xiong, Ming-Feng,Zhang, Hao,Shi, Lei,Lin, Dong-Zi,Liu, Hai-Yang
, p. 1541 - 1548 (2021/04/21)
Copper porphyrin-catalyzed construction of C(sp2)—O bond via coupling formamides with phenols was achieved firstly. A broad range of substrates afforded various carbamates in moderate to good yields with good functional group tolerance at low catalyst loading. Intermolecular competing kinetic isotope effect experiment indicated that the generation of formamide radical is the rate-determining step of current cross-dehydrogenative coupling (CDC) reaction. The research extends the application of metalloporphyrin in CDC reaction.
Electrochemically Catalyzed Newman-Kwart Rearrangement: Mechanism, Structure-Reactivity Relationship, and Parallels to Photoredox Catalysis
Roesel, Arend F.,Ugandi, Mihkel,Huyen, Nguyen Thi Thu,Májek, Michal,Broese, Timo,Roemelt, Michael,Francke, Robert
, p. 8029 - 8044 (2020/07/25)
The facilitation of redox-neutral reactions by electrochemical injection of holes and electrons, also known as "electrochemical catalysis", is a little explored approach that has the potential to expand the scope of electrosynthesis immensely. To systematically improve existing protocols and to pave the way toward new developments, a better understanding of the underlying principles is crucial. In this context, we have studied the Newman-Kwart rearrangement of O-arylthiocarbamates to the corresponding S-aryl derivatives, the key step in the synthesis of thiophenols from the corresponding phenols. This transformation is a particularly useful example because the conventional method requires temperatures up to 300 °C, whereas electrochemical catalysis facilitates the reaction at room temperature. A combined experimental-quantum chemical approach revealed several reaction channels and rendered an explanation for the relationship between the structure and reactivity. Furthermore, it is shown how rapid cyclic voltammetry measurements can serve as a tool to predict the feasibility for specific substrates. The study also revealed distinct parallels to photoredox-catalyzed reactions, in which back-electron transfer and chain propagation are competing pathways.
Room-temperature Pd-catalyzed C-H chlorination by weak coordination: One-pot synthesis of 2-chlorophenols with excellent regioselectivity
Sun, Xiuyun,Sun, Yonghui,Zhang, Chao,Rao, Yu
supporting information, p. 1262 - 1264 (2014/02/14)
A room-temperature Pd(ii)-catalyzed regioselective chlorination reaction has been developed for a facile one-pot synthesis of a broad range of 2-chlorophenols. The reaction demonstrates an excellent regioselectivity and reactivity for C-H chlorination. This reaction represents one of the rare examples of mild C-H functionalization at ambient temperature.
A general approach towards catechol and pyrogallol through ruthenium- and palladium-catalyzed C-H hydroxylation by weak coordination
Yang, Xinglin,Sun, Yonghui,Chen, Zhang,Rao, Yu
supporting information, p. 1625 - 1630 (2014/06/09)
An efficient ruthenium(II)- and palladium(II)-catalyzed C-H hydroxylation of aryl carbamates has been developed for the facile synthesis of catechols and pyrogallols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by a gram-scale synthesis.
Palladium catalyzed C-H functionalization of O-arylcarbamates: Selective ortho -bromination using NBS
John, Alex,Nicholas, Kenneth M.
experimental part, p. 5600 - 5605 (2012/07/30)
A series of cyclometalated palladium complexes derived from O-phenylcarbamates has been synthesized by the reaction of the respective carbamates with Pd(OAc)2 in the presence of acids, CF 3CO2H, CF3SO3/sub
Infrared Spectra and Transmission of Electronic Effects in Substituted Phenyl N,N-Dimethylcarbamates and S-Phenyl N,N-Dimethylthiocarbamates
Perjessy, Alexander,Jones, Ronald G.,McClair, Susan L.,Wilkins, Joyce M.
, p. 1266 - 1271 (2007/10/02)
Carbonyl stretching frequencies in CCl4 and CHCl3 and hydroxyl stretching frequency shifts of phenol as a proton donor in CCl4 were measured for series of substituted phenyl N,N-dimethylcarbamates (I) and S-phenyl N,N-dimethylthiocarbamates (II).The data
