1380424-47-4Relevant academic research and scientific papers
Palladium-catalyzed highly regioselective Mizoroki-heck arylation of allylamines with aryl chlorides
Zhang, Lingjuan,Jiang, Zhen,Dong, Chaonan,Xue, Xiao,Qiu, Ruiying,Tang, Weijun,Li, Huanrong,Xiao, Jianliang,Xu, Lijin
, p. 311 - 318 (2014/01/23)
Palladium catalyst systems for the regioselective Mizoroki-Heck arylation of N,N-diprotected and N-protected allylamines with aryl chlorides have been developed. Pd(OAc)2 in combination with appropriate additives could efficiently catalyze the linear arylation of N,N-diprotected allylamines with aryl chlorides in toluene to give exclusively the γ-arylated products in good to excellent yields and with excellent regio- and stereocontrol and good functional group tolerance. With use of a catalytic mixture of Pd(OAc) 2 and 1,1'-bis(diphenylphosphino)ferrocene, the arylation of N-protected allylamines with aryl chlorides could be accomplished in ethylene glycol/DMSO, which afforded complete β-regioselectivity with good functional group tolerance. The steric and electronic properties of allylamine substrates are found to be critical to the catalytic activity and regiocontrol in both linear and internal arylations. Copyright
Palladium-catalyzed regioselective and stereoselective oxidative heck arylation of allylamines with arylboronic acids
Zhang, Lingjuan,Dong, Chaonan,Ding, Chenjun,Chen, Jing,Tang, Weijun,Li, Huanrong,Xu, Lijin,Xiao, Jianliang
supporting information, p. 1570 - 1578 (2013/06/27)
A general and convenient palladium-catalyzed oxidative Heck arylation of both N-protected and N,N-diprotected allylic amines with arylboronic acids under mild conditions has been developed. The catalyst system, consisting of Pd(OAc)2 (palladium acetate), AgOAc (silver acetate) and KHF 2 (potassium hydrogen fluoride), could efficiently catalyze the coupling reaction in acetone without the aid of any ligand, leading exclusively to the γ-arylated allylic amine products in good to excellent yields. This method is highlighted with excellent regio- and stereocontrol and remarkable functional group tolerance. The carbamate moiety in allylic amine substrates is of crucial importance to the catalytic performance, and the chelation between the carbonyl O (oxygen) and Pd (palladium) atoms is believed to be responsible for the high regioselectivity and stereoselectivity observed. Copyright
