115270-07-0Relevant articles and documents
β-regioselective intermolecular Heck arylation of N,N-disubstituted allylamines
Wu,Marcoux,Davies,Reider
, p. 159 - 162 (2001)
β-Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary β-aryl allyl amines.
Covalent Organic Framework as a Heterogeneous Ligand for the Regioselective Oxidative Heck Reaction
Han, Jiyao,Sun, Xiaowei,Wang, Xiao,Wang, Qiong,Hou, Shenghuai,Song, Xin,Wei, Yingqin,Wang, Rongyu,Ji, Wenhua
supporting information, p. 1480 - 1484 (2020/03/13)
A simple imine-based covalent organic framework (COF) as heterogeneous ligand for PdII-promoted Heck reaction is reported. Good regioselectivity for a wide range of electronically unbiased olefins is obtained (linear/branched >100:1 in most cases). Related tests and density functional theory calculations are used to explore the reason underlying the high selectivity. This research opens a route for COF as an intriguing platform to control regioselectivity catalysis.
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