589-09-3Relevant articles and documents
Preparation and Coordination Properties Including Catalytic Activities of a Bulky 2-Methyl-3-thioxo-1,3-diphosphapropene
Liang, Hongze,Ito, Shigekazu,Yoshifuji, Masaaki
, p. 425 - 427 (2004)
(Matrix presented) 2-Methyl-3,3-diphenyl-3-thioxo-1-(2,4,6-tri-tert- butylphenyl)-1,3-diphosphapropene, which bears a P=C-P=S skeleton, was prepared and used as a ligand of transition-metal complexes. The palladium complexes containing the ligated 3-thioxo-1,3-diphophapropene were stable and used for catalytic reactions such as cross-couplings and direct conversion of allyl alcohol to allylaniline.
Copper-Catalyzed Allylation of Amines with Cyclopropyldiphenylsulfonium Trifluoromethanesulfonate
Ma, Yu,Tian, Ze-Yu,Zhang, Cheng-Pan,Zheng, Shuang-Yang
, (2022/03/15)
Cyclopropyldiphenylsulfonium salt, a famous ylide precursor previously extensively employed in the preparation of cyclic compounds, has been successfully utilized as an efficient allylation reagent in this work. The copper-catalyzed reactions of cyclopropyldiphenylsulfonium trifluoromethanesulfonate with amines in the presence of an appropriate ligand provided the N-allylated products in good yields. Aliphatic/ aromatic amines and primary/secondary amines were all converted under mild reaction conditions. This protocol was also applicable to N-functionalization of drug molecules, supplying the corresponding N-allylated compounds in satisfactory yields. The reaction, which showed good functional group tolerance with a wide range of substrates and excellent chemoselectivity, offers an interesting method for the synthesis of N-allyl amines.
Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
supporting information, p. 9355 - 9360 (2021/07/19)
The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
Nickel-Catalyzed Aminofluoroalkylation of Alkenes: Access to Difluoroalkylated N-Containing Heterocyclic Compounds
Fu, Xiaoyi,Sun, Yijie,Wu, Fanhong,Wu, Jingjing,Zhang, Tianyu
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.
