97637-73-5Relevant articles and documents
Development of a CuCl/phosphine system to catalyze phenylation and methylation of N-tosyl aldimines with phenylboronic andmethylboronic acids
Ashouri, Akram,Nasiri, Behzad,Pourian, Somayeh,Samadi, Saadi,Zamani, Hossein
, p. 575 - 581 (2021/01/13)
The addition of phenylboronic and methylboronic acids to activated aromatic aldimines was demonstrated in the presence of copper(I)-phosphine complexes. The desired products were obtained using copper chloride/phosphine, and potassium fluoride in under toluene reflux, in moderate-to-good yield and a suitable reaction time.
Site-Selective Electrochemical Benzylic C?H Amination
Hou, Zhong-Wei,Liu, Ding-Jin,Xiong, Peng,Lai, Xiao-Li,Song, Jinshuai,Xu, Hai-Chao
supporting information, p. 2943 - 2947 (2020/12/11)
C?H/N-H cross-coupling is an ideal strategy to synthesize various amines but remains challenging owing to the requirement for sacrificial chemical oxidants and the difficulty in controlling the regio- and chemo-selectivity. Herein we report a site-selective electrochemical amination reaction that can convert benzylic C?H bonds into C-N linkages via H2 evolution without need for external oxidants or metal catalysts. The synthetic strategy involves anodic cleavage of benzylic C?H to form a carbocation intermediate, which is then trapped with an amine nucleophile leading to C?N bond formation. Key to the success is to include HFIP as a co-solvent to modulate the oxidation potentials of the alkylbenzene substrate and the aminated product to avoid overoxidation of the latter.
Redox Self-Adaptation of a Nitrene Transfer Catalyst to the Substrate Needs
Gouré, Eric,Senthilnathan, Dhurairajan,Coin, Guillaume,Albrieux, Florian,Avenier, Frédéric,Dubourdeaux, Patrick,Lebrun, Colette,Maldivi, Pascale,Latour, Jean-Marc
supporting information, p. 4305 - 4309 (2017/04/04)
The development of iron catalysts for carbon–heteroatom bond formation, which has attracted strong interest in the context of green chemistry and nitrene transfer, has emerged as the most promising way to versatile amine synthetic processes. A diiron system was previously developed that proved efficient in catalytic sulfimidations and aziridinations thanks to an FeIIIFeIV active species. To deal with more demanding benzylic and aliphatic substrates, the catalyst was found to activate itself to a FeIIIFeIVL. active species able to catalyze aliphatic amination. Extensive DFT calculations show that this activation event drastically enhances the electron affinity of the active species to match the substrates requirements. Overall this process consists in a redox self-adaptation of the catalyst to the substrate needs.
