22774-76-1Relevant articles and documents
Nickel-Catalyzed Aminofluoroalkylation of Alkenes: Access to Difluoroalkylated N-Containing Heterocyclic Compounds
Fu, Xiaoyi,Zhang, Tianyu,Wu, Jingjing,Sun, Yijie,Wu, Fanhong
supporting information, (2021/12/03)
A nickel-catalyzed aminofluoroalkylative cyclization of unactive alkenes with iododifluoromethyl ketones was developed to construct versatile difluoroalkylated Nitrogen-containing heterocycles including aziridines, pyrrolidines and piperidines in moderate to high yields. This method features a broad substrate scope and has been demonstrated on gram scale.
A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols
Sweeney, Joseph B.,Ball, Anthony K.,Lawrence, Philippa A.,Sinclair, Mackenzie C.,Smith, Luke J.
supporting information, p. 10202 - 10206 (2018/08/06)
The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).
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