145909-49-5Relevant academic research and scientific papers
Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
Du, Yangxu,Hou, Jiao,Lu, Qing,Hao, Wei,Yu, Wenquan,Chang, Junbiao
, 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
Molecular Oxygen-Mediated Radical Alkylation of C(sp3)-H Bonds with Boronic Acids
Yang, Le,Qiu, Zhihong,Wu, Jintao,Zhao, Jianyou,Shen, Tong,Huang, Xuan,Liu, Zhong-Quan
, p. 3207 - 3210 (2021/05/04)
A direct and site-specific alkylation of (sp3)C-H bond with aliphatic boronic acid was achieved. By simply heating glycinates and amines together with alkylboronic acids under an oxygen atmosphere, a variety of unnatural α-amino acids and peptides could b
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.
Chiral Br?nsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane
Skrypai, Vladislav,Varjosaari, Sami E.,Azam, Fawwaz,Gilbert, Thomas M.,Adler, Marc J.
, p. 5021 - 5026 (2019/05/10)
The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Br?nsted acid catalyst is reported. This is the first known example of chiral Br?nsted acid-catalyzed asymmetric reductive amination using
Efficient one-pot alkylation of imines using nanosilver iodide in aqueous media
Safaei-Ghomi, Javad,Kakavand-Qalenoei, Ahmad,Ghasemzadeh, Mohammad Ali,Salavati-Niasari, Masoud
, p. 852 - 859 (2013/02/22)
An efficient ecofriendly method for the alkylation reaction of various imines is described by a simple one-pot reaction of aldehydes, amines and alkyl iodides in the presence of AgI nanoparticles in aqueous media. Silver iodide nanoparticles mediated an e
Electrochemical allylation reactions of simple imines in aqueous solution mediated by nanoscale zinc architectures
Huang, Jing-Mei,Wang, Xu-Xiao,Dong, Yi
experimental part, p. 924 - 927 (2011/03/20)
I zinc we're alone now: The title reactions were achieved in an undivided cell fitted with a pair of zinc electrodes in aqueous solution. A preliminary study on the relationship of reaction activity and surface morphology showed that the deposited zinc powders with nanoscale architectures had very high activity.
Zinc(II)-catalyzed addition of grignard reagents to ketones
Hatano, Manabu,Ito, Orie,Suzuki, Shinji,Ishihara, Kazuaki
supporting information; experimental part, p. 5008 - 5016 (2010/10/04)
(Figure presented) The addition of organometallic reagents to carbonyl compounds has become a versatile method for synthesizing tertiary and secondary alcohols via carbon-carbon bond formation. However, due to the lack of good nucleophilicity or the presence of strong basicity of organometallic reagents, the efficient synthesis of tertiary alcohols from ketones has been particularly difficult and, thus, limited. We recently developed highly efficient catalytic alkylation and arylation reactions to ketones with Grignard reagents (RMgX: R = alkyl, aryl; X = Cl, Br, I) using ZnCl2, Me3SiCH 2MgCl, and LiCl, which effectively minimize problematic side reactions. In principle, RMgBr and RMgI are less reactive than RMgCl for the addition to carbonyl compounds. Therefore, this novel method with homogeneous catalytic ZnCl2·Me3SiCH2MgCl·LiCl is quite attractive, since RMgBr and RMgI, which are easily prepared and/or commercially available, like RMgCl, can be applied successfully. As well as ketones and aldehydes, aldimines were effectively applied to this catalysis, and the corresponding secondary amines were obtained in high yield. With regard to mechanistic details concerning β-silyl effect and salt effect, in situ-prepared [R(Me3SiCH2)2Zn] -[Li]+[MgX2]m[LiCl]n (X = Cl/Br/I) is speculated to be a key catalytic reagent to promote the reaction effectively. The simplicity of this reliable ZnCl2·Me 3SiCH2MgCl·LiCl system in the addition of Grignard reagents to carbonyl compounds might be attractive for industrial as well as academic applications.
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
Indium (Zinc)-copper-mediated barbier-type alkylation reaction of nitrones in water: Synthesis of amines and hydroxylamines
Yang, Yong-Sheng,Shen, Zhi-Liang,Loh, Teck-Peng
supporting information; experimental part, p. 1209 - 1212 (2009/08/07)
An efficient method for the Barbier-type alkylation reaction of various nitrones (including chiral version) and alkyl halides in water is described. The amines and hydroxylamines can be obtained in good yields, depending on the judicious choice of the metal complexes used.
Indium-silver- and zinc-silver-mediated barbier-grignard-type alkylation reactions of imines by using unactivated alkyl halides in aqueous media
Shen, Zhi-Liang,Cheong, Hao-Lun,Loh, Teck-Peng
experimental part, p. 1875 - 1880 (2009/04/06)
In the presence of In or Zn/AgI/InCl3, an efficient and practical method for the Barbier-Grignard-type alkylation reactions of simple imines by using a one-pot condensation of various aldehydes, amines (including the aliphatic and chiral version), and secondary alkyl iodides has been developed. The reaction proceeded more efficiently in water than in organic solvents. Without the use of CuI, it mainly gave the imine self-reductive coupling product, which was not the alkylated product. Good diastereoselectivities (up to 92:8 dr) were obtained when L-valine methyl ester was used as the substrate.
