3532-71-6Relevant academic research and scientific papers
Manganese-catalyzed [3 + 2] cyclization of ketones and isocyanates via inert C-H activation
Huo, Jiaqi,Wang, Congyang,Yang, Yunhui
supporting information, p. 3384 - 3388 (2021/05/29)
Stoichiometric cyclomanganation of aromatic ketones and further reactions of the thus-formed manganacycles with isocyanates were first reported by Kaesz and Liebeskind in 1975 and 1990, respectively. The buildup of a closed manganese catalytic cycle for the reaction of ketones and isocyanates remains an unsolved problem. Herein, an unprecedented trio of Me2Zn/AlCl3/AgOTf is developed to build up manganese catalysis, which enables the [3 + 2] cyclization of ketones with isocyanates via inert C-H activation to access 3-alkylidene phthalimidines in a straightforward manner unachieved by other transition metal catalyses.
Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones
Nozawa-Kumada, Kanako,Matsuzawa, Yuta,Ono, Kanako,Shigeno, Masanori,Kondo, Yoshinori
, p. 8604 - 8607 (2021/09/02)
A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp3)-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp3)-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp3)-H bonds and shows excellent functional group tolerance. This journal is
Eosin Y as a Redox Catalyst and Photosensitizer for Sequential Benzylic C?H Amination and Oxidation
Yan, Dong-Mei,Zhao, Quan-Qing,Rao, Li,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 16895 - 16901 (2018/10/26)
A new synergistic multicatalytic activation mode of eosin Y has been discovered by exploiting the redox potential of its ground state and excited state. This catalytic strategy proves to be an enabling tool for visible-light-driven sequential benzylic C?H amination and oxidation of o-benzyl-N-methoxyl-benzamides when using Selectfluor as a hydrogen atom transfer (HAT) reagent and O2 as oxidant. Efficient synthesis of a range of diversely functionalized 3-hydroxyisoindolinones can thus be achieved with good yields and selectivity at mild reaction conditions. Preliminary mechanistic studies and DFT calculations suggest that eosin Y works as a redox catalyst and photosensitizer.
Preparation of 3-Hydroxyindolin-1-ones and o-Acylbenzamides. A Study of Ring-Chain Tautomerism
Nishio, Takehiko,Yamamoto, Hiroshi
, p. 883 - 892 (2007/10/02)
3-Hydroxyisoindolinones (ring form) as well as their chain tautomers, o-acylbenzamides, were prepared from the reactions of 3-benzalphthalide 1, 3-halophthalides 3, and o-acylbenzoic acids 6 or their esters 7 with amines 2, and those of phthalimides 4 wit
Reaction of N-Arylphthalisoimidium Perchlorates with Amines and Aromatic Hydrocarbons under Friedel-Crafts Conditions, a New and Convenient One-Step Method for the Synthesis of 2,3-Diaryl-3-hydroxyphthalimidines
Ismail, M. Fekry,Enayat, E. I.,El-Bassiouny, F. A.,Younes, H. A.
, p. 707 - 710 (2007/10/02)
N-Arylphthalisoimidium perchlorates (1a, b) react with primary amines via ring-opening to give N,N'-disubstituted phthalamides (3a-d).They react with aromatic hydrocarbons under Friedel-Crafts conditions to give 2,3-diaryl-3-hydroxyphthalimidines (a-i) while the reaction of 1a wtith phenylmagnesium bromide involved just deprotonation to the isoimide (9) followed by rearrangement to N-phenylphthalimide (8).
