95106-72-2Relevant academic research and scientific papers
ZnI2-Catalyzed Aminotrifluoromethylation Cyclization of Alkenes Using PhICF3Cl
Huang, Wanqiao,Xu, Cong,Yu, Jianxin,Wang, Mang
, p. 1987 - 1999 (2021/02/05)
We report here an alternatively catalytic aminotrifluoromethylation of alkenes using PhICF3Cl as a bifunctional reagent along with ZnI2 as a dual catalyst. A combined catalytic strategy was established for the intramolecular aminotrifluoromethylation of 4-pentenamines. As a result, a set of 2-trifluoroethyl-pyrrolidines was obtained in a high selectivity. Mechanism studies revealed that the reaction included an iodine anion-catalyzed radical chlorotrifluoromethylation of alkenes and a sequential Lewis acid-promoted aminocyclization of the resulting chlorotrifluoromethylated intermediates.
Copper-Catalyzed Carbonylative Synthesis of β-Homoprolines from N-Fluoro-sulfonamides
Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan
supporting information, p. 1889 - 1893 (2020/03/24)
A new methodology for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramolecular cyclization and intermolecular carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive molecules.
Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6- endo Aminoacetoxylation of Unactivated Alkenes
Qi, Xiaoxu,Chen, Chaohuang,Hou, Chuanqi,Fu, Liang,Chen, Pinhong,Liu, Guosheng
supporting information, p. 7415 - 7419 (2018/06/08)
A novel asymmetric 6-endo aminoacetoxylation of unactivated alkenes by palladium catalysis, which yields chiral β-acetoxylated piperidines with excellent chemo-, regio- and enantioselectivities under very mild reaction conditions, has been established herein by employing a new designed pyridine-oxazoline (Pyox) ligand. Importantly, introducing a sterically bulky group into the C-6 position of Pyox is crucial to enhance the reactivity of the aminoacetoxylation of alkenes.
Thioamination of Alkenes with Hypervalent Iodine Reagents
Mizar, Pushpak,Niebuhr, Rebecca,Hutchings, Matthew,Farooq, Umar,Wirth, Thomas
supporting information, p. 1614 - 1617 (2016/02/20)
An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2-aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.
MCPBA-mediated metal-free intramolecular aminohydroxylation and dioxygenation of unfunctionalized olefins
Liu, Gong-Qing,Li, Lin,Duan, Lili,Li, Yue-Ming
, p. 61137 - 61143 (2015/08/03)
mCPBA-mediated metal-free intramolecular aminohydroxylation and dioxygenation reactions of unfunctionalized olefins are reported. In the presence of 1.2 equiv. of m-chlorobenzoic peracid, different N-sulfonyl 4-penten-1-amine substrates could be cyclized
Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes
Zhang, Zuxiao,Tang, Xiaojun,Thomoson, Charles S.,Dolbier, William R.
supporting information, p. 3528 - 3531 (2015/07/28)
A photoredox catalyzed aminodifluoromethylation of unactivated alkenes has been developed in which HCF2SO2Cl is used as the HCF2 radical source. Sulfonamides were active nucleophiles in the final step of a tandem addition/oxidation/cyclization process to form pyrrolidines, and esters were found to cyclize to form lactones. Thus, a variety of pyrrolidines and lactones were obtained in moderate to excellent yield. In order for the cyclization reactions to be efficient, a combination of a copper catalyst (Cu(dap)2Cl) and silver carbonate was crucial to suppressing a competing chloro, difluoroalkylation process.
Cu(oac)2-promoted cascade carboamination/oxidative cyclization of c-acylimines with alkenes
Dang, Ling,Liang, Libo,Qian, Cheng,Fu, Meiqin,Ma, Tongmei,Xu, Dingguo,Jiang, Huanfeng,Zeng, Wei
, p. 769 - 776 (2014/04/03)
A Cu(OAc)2-promoted cascade carboamination/oxidative cyclization of alkenes with a-imino esters has been explored. This transformation provides a concise approach to rapid assembly of 2-oxo-3-iminopyrrole derivatives in moderate to good yields.
Organocatalytic Stereoselective Iodoamination of Alkenes
Mizar, Pushpak,Burrelli, Alessandra,Günther, Erika,S?ftje, Martin,Farooq, Umar,Wirth, Thomas
supporting information, p. 13113 - 13116 (2016/02/19)
A new chiral thiohydantoin catalyst is used for the stereoselective iodoamination of alkenes. N-iodosuccinimide as the source of the electrophilic iodine is activated by catalytic amounts of different additives which also influence the regioselectivity of some cyclizations.
Efficient copper-catalyzed direct intramolecular aminotrifluoromethylation of unactivated alkenes with diverse nitrogen-based nucleophiles
Lin, Jin-Shun,Xiong, Ya-Ping,Ma, Can-Liang,Zhao, Li-Jiao,Tan, Bin,Liu, Xin-Yuan
supporting information, p. 1332 - 1340 (2014/04/03)
A mild, convenient, and step-economical intramolecular aminotrifluoromethylation of unactivated alkenes with a variety of electronically distinct, nitrogen-based nucleophiles in the presence of a simple copper salt catalyst, in the absence of extra ligand
Regioselective copper(II)-mediated bromoamination of unfunctionalized olefins: An efficient route to N-heterocyclic compounds
Liu, Gong-Qing,Ding, Zhen-Ying,Zhang, Li,Li, Ting-Ting,Li, Lin,Duan, Lili,Li, Yue-Ming
supporting information, p. 2303 - 2310 (2014/07/21)
Bromoamination of unfunctionalized olefins was realized under mild conditions using copper(II) bromide (CuBr2) as both reaction promoter and bromine source. The reactions could be carried out under open air at ambient temperature, and both N-alkylated and N-tosylated substrates could be converted to the corresponding N-heterocyclic compounds in high regioselectivity and good isolated yields. A variety of biologically important structures could be obtained via subsequent nucleophilic substitution reactions.
