80865-90-3Relevant academic research and scientific papers
Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
Chang, Junbiao,Du, Yangxu,Hao, Wei,Hou, Jiao,Lu, Qing,Yu, Wenquan
, p. 16223 - 16226 (2021/09/22)
An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary ami
Iron-catalysed 1,2-aryl migration of tertiary azides
Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
, p. 11685 - 11688 (2020/10/19)
1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
Remote sp3 C–H Amination of Alkenes with Nitroarenes
Xiao, Jichao,He, Yuli,Ye, Feng,Zhu, Shaolin
supporting information, p. 1645 - 1657 (2018/05/16)
Direct installation of a functional group at remote, unfunctionalized sites in an alkyl chain is a synthetically valuable but rarely reported process. The remote relay hydroarylamination of distal and proximal olefins, and of olefin isomeric mixtures, has been achieved through NiH-catalyzed alkene isomerization and sequential reductive hydroarylamination with nitroarenes. This provides an attractive approach to the direct installation of a distal arylamino group within alkyl chains. The single-step conversion of simple olefins and nitro(hetero)arenes to value-added arylamines is a practical strategy for amine synthesis as well as the remote activation of sp3 C–H bonds. The value of this transformation is further supported by the regioconvergent arylamination of isomeric mixtures of olefins. Modern organic synthesis requires more efficient strategies, such as C–H functionalization, with which to construct complex molecules from readily available chemicals. Undirected functionalization of remote aliphatic C–H bonds is a synthetically valuable but largely unknown process. Synergistic combination of metal-catalyzed chainwalking (migration of a double bond along the hydrocarbon chain, a process involving repeated migratory insertions and β-hydride eliminations) and cross-coupling chemistry offers a general approach to the remote functionalization of easily accessed unsaturated hydrocarbon substrates. In this paper, we demonstrate that direct installation of a distal arylamino group can be achieved from two common feedstock chemicals (olefins and nitroarenes) via nickel hydride chemistry. It is anticipated that the strategy could inspire the development of other remote functionalizations with different regioselectivity as well as asymmetric transformations. Zhu and colleagues describe the remote hydroamination of alkenes with nitro(hetero)arenes through nickel-catalyzed alkene isomerization and sequential reductive relay hydroamination process. Using two common feedstock chemicals, olefins and nitroaromatics, in an operationally simple procedure, this attractive protocol provides efficient and practical access to a wide range of arylamines under mild conditions.
Umpolung Addition of Aldehydes to Aryl Imines
Chen, Ning,Dai, Xi-Jie,Wang, Haining,Li, Chao-Jun
, p. 6260 - 6263 (2017/05/19)
One of the classical ways to synthesize amines involves the coupling of carbonyl compounds and imines, either through enolate chemistry or acyl-based carbanion equivalents. We herein report an alternative strategy that is based on the use of aldehydes as alkyl carbanion equivalents in a reductive coupling with aryl imines. A wide array of secondary amines can be synthesized in moderate to high yields. This reaction is mediated by hydrazine and catalyzed by ruthenium(II) complexes, and it tolerates various functional groups, such as esters, amides, and nitriles.
Catalytic reactions of titanium alkoxides with Grignard reagents and imines: A mechanistic study
Kumar, Akshai,Samuelson, Ashoka G.
experimental part, p. 1830 - 1837 (2011/04/25)
The reactivity of Grignard reagents towards imines in the presence of catalytic and stoichiometric amounts of titanium alkoxides is reported. Alkylation, reduction, and coupling of imines take place. Whereas reductive coupling is the major reaction in sto
Triazole-Au(I) complexes: A new class of catalysts with improved thermal stability and reactivity for intermolecular alkyne hydroamination
Duan, Haifeng,Sengupta, Sujata,Petersen, Jeffrey L.,Akhmedov, Novruz G.,Shi, Xiaodong
supporting information; experimental part, p. 12100 - 12102 (2009/12/30)
(Chemical Equation Presented) A series of 1,2,3-triazole-bound cationic Au(I) catalysts have been synthesized, and their structures have been characterized by X-ray crystallography. Variable-temperature NMR studies revealed dynamic triazole-Au cation coor
TiCl4-catalyzed indirect anti-Markovnikov hydration of alkynes: Application to the synthesis of benzo[b]furans
Ackermann, Lutz,Kaspar, Ludwig T.
, p. 6149 - 6153 (2008/02/09)
(Chemical Equation Presented) An efficient methodology for the indirect anti-Markovnikov hydration of unsymmetrically substituted terminal and internal alkynes is based on TiCl4-catalyzed hydroamination reactions. Its application to ortho-alkynylhaloarenes, followed by a copper-catalyzed O-arylation, provides flexible access to substituted benzo[b]furans.
Highly efficient alkylation to ketones and aldimines with Grignard reagents catalyzed by zinc(II) chloride
Hatano, Manabu,Suzuki, Shinji,Ishihara, Kazuaki
, p. 9998 - 9999 (2007/10/03)
A highly efficient alkylation to ketones and aldimines with Grignard reagents in the presence of catalytic trialkylzinc(II) ate complexes derived from ZnCl2 (10 mol %) in situ was developed. This simple Zn(II)-catalyzed alkylation could minimize the well-known but serious problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved. Copyright
