1495-59-6Relevant academic research and scientific papers
Chelation-assisted C-N cross-coupling of phosphinamides and aryl boronic acids with copper powder at room temperature
Peng, Yao,Lei, Jian,Qiu, Renhua,Peng, Lingteng,Au, Chak-Tong,Yin, Shuang-Feng
, p. 4065 - 4070 (2018)
A protocol for the chelation-assisted C-N cross-coupling of phosphinamides and aryl boronic acids with copper powder under an oxygen atmosphere is reported. This reaction proceeds efficiently to afford fully substituted unsymmetrical N-arylation phosphinamides at room temperature in excellent yields. Diverse unstable functional groups on the benzene ring of aryl boronic acids such as vinyl, formyl, acetyl, sulfonyl, acetylamino, cyano, nitro, and trifluoromethyl can be accommodated.
Copper-Catalyzed Oxidative C(sp3)?H/N?H Cross-Coupling of Hydrocarbons with P(O)?NH Compounds: the Accelerating Effect Induced by Carboxylic Acid Coproduct
Lei, Jian,Yang, Yincai,Peng, Lingteng,Wu, Lesong,Peng, Ping,Qiu, Renhua,Chen, Yi,Au, Chak-Tong,Yin, Shuang-Feng
supporting information, p. 1689 - 1696 (2019/03/07)
An chelation-assisted oxidative C(sp3)?H/N?H cross coupling of hydrocarbons with P(O)?NH compounds using copper acetate as catalyst is described. The results of kinetic experiments, mechanistic studies and DFT calculations demonstrate the importance of acetic acid coproduct as an additive for promoting the formation of intermediate bis((diphenylphosphoryl)(quinolin-8-yl)amino)copper (6), and consequently accelerating the construction of C(sp3)?N bond. The reaction proceeded efficiently with a wide array of hydrocarbons and P(O)?NH compounds, and the rate acceleration induced by the acetic acid coproduct have been repeatedly proven. Furthermore, the efficiency of small-scale reaction could be retained upon gram-scale synthesis in a continuous manner. (Figure presented.).
