21299-15-0Relevant academic research and scientific papers
Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl: Tert -butyl ether as a new methylene precursor
Jin, Jiang,Li, Yinghua,Xiang, Shiqun,Fan, Weibin,Guo, Shiwei,Huang, Deguang
, p. 4076 - 4081 (2021/05/19)
A novel, green and efficient method is developed for the synthesis of methylene bridged bis(indolyl)methanes in good to excellent yields. The reaction employs methyl tert-butyl ether (MTBE) as the methylene source and selectfluor as an oxidizing agent. The scope and versatility of the methods have been successfully demonstrated with 48 examples. The metal-free transformation process is suitable for scale-up production. A selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies. This journal is
Diamine-mediated degradative dimerisation of Morita-Baylis-Hillman ketones
Jha, Ajit Kumar,Kumari, Anju,Easwar, Srinivasan
supporting information, p. 2949 - 2952 (2020/03/18)
A degradative dimerisation of Morita-Baylis-Hillman ketones was observed in the presence of a primary diamine. The reaction proceeded swiftly to produce methylene-bridged 1,3-dicarbonyl compounds. A brief mechanistic investigation alluded to a retro-Mannich reaction as the key step of the transformation.
Synthesis of Hexahydropyrimidines and 1,2,3,4-Tetrahydropyridines by Reaction of Ethyl Benzoylacetate with Formaldehyde and Primary Amines
Kamalova, A. I.,Kireeva, D. R.
, p. 1733 - 1737 (2020/12/01)
Abstract: The reaction of ethyl benzoylacetate with formaldehyde and primary amines in boiling pyridine or methanol afforded new 1,2,3,4-tetrahydropyridine derivatives and substituted hexahydropyrimidines.
Metal-free Csp3-N bond cleavage of amides using tert-butyl hydroperoxide as oxidant
Guo, Shengmei,Zhu, Zheng,Lu, Lin,Zhang, Wenbiao,Gong, Jiuhan,Cai, Hu
, p. 543 - 546 (2015/05/12)
A mild and efficient protocol for the metal-free C-N bond-cleavage of amides has been developed. The methodology employs iodine as a catalyst to cleave the C(Me)-N bond of dimethylformamide or dimethylacetamide, providing novel access to methylene-bridged bis-1,3-dicarbonyl compounds instead of enol carbamates in the presence of tert-butyl hydroperoxide.
Metal-free synthesis of methylene-bridged bis-1,3-dicarbonyl compounds via oxidative C-C bond cleavage of tertiary aliphatic amines
Xing, Li-Juan,Wang, Xi-Mei,Li, Hong-Ying,Zhou, Wen,Kang, Ning,Wang, Peng,Wang, Bin
, p. 26783 - 26786 (2014/07/21)
A metal-free Bu4NI mediated oxidative reaction utilizing tertiary aliphatic amines and 1,3-dicarbonyl compounds for the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds has been developed. This reaction involved an unexpected C-C bond cleavage of tertiary aliphatic amines. With this approach, the completely regioselective functionalization of β-carbon on tertiary amines was realized. This journal is the Partner Organisations 2014.
Visible-light photoredox-mediated oxidation of N-methyl tertiaryamines under catalyst free conditions: Direct synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
Dai, Xiao-Jun,Xu, Xiao-Liang,Cheng, Dong-Ping,Li, Xiao-Nian
supporting information, p. 545 - 548 (2014/05/06)
Mediated by visible light-induced photoredox catalysis and free of other catalysts, a new and efficient synthesis of methylene-bridged bis-1,3-dicarbonyl derivatives has been developed. A variety of N-methyl tertiaryamines and 1,3-dicarbonyl compounds were investigated in this reaction.
Oxidative C(Sp3)-H activation and C-N cleavage of N-methyl amines under transition-metal-free condition for synthesis of methylene-bridged bis-1,3-diketones
Wang, Xiaohu,Wang, Yi,Yuan, Yu,Xing, Chun-Hui
, p. 2195 - 2202 (2014/03/21)
A transition-metal-free oxidative methylenation reaction was developed. Methylene-bridged bis-1,3-dicarbonyl compounds were synthesized by oxidative C(Sp3)-H activation and C-N cleavage of N-methyl amines. This novel reaction avoids the use of
Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: Synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
Zhao, Dan,Wang, Yue,Zhu, Min-Xue,Shen, Qi,Zhang, Lei,Du, Yun,Li, Jian-Xin
, p. 10272 - 10276 (2013/09/02)
A green, simple, and efficient protocol for the selective methylenation via CuCl2/oxygen-mediated C-H (sp3) oxidation and C-N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored. The Royal Society of Chemistry 2013.
Aerobic oxidation of a tertiary aliphatic amine under visible-light photocatalysis: Facile synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
Yoo, Woo-Jin,Tanoue, Arata,Kobayashi, Shu
, p. 2764 - 2767 (2013/02/22)
Lights, camera, action! An efficient protocol for the formation of methylene-bridged bis-1,3-dicarbonyl compounds has been developed through an aerobic photocatalytic oxidative coupling reaction between 1,3-dicarbonyl compounds and a tertiary aliphatic amine. Copyright
Iron-catalyzed oxidation of tertiary amines: Synthesis of β-1,3-dicarbonyl aldehydes by three-component C-C couplings
Liu, Weiping,Liu, Jinhua,Ogawa, Daisuke,Nishihara, Yasushi,Guo, Xingwei,Li, Zhiping
supporting information; experimental part, p. 6272 - 6275 (2012/01/06)
β-1,3-Dicarbonyl aldehydes were synthesized by iron-catalyzed oxidative reactions between 1,3-dicarbonyl compounds and two molecules of tertiary amines in the presence of tert-butyl hydroperoxide (TBHP). α,β-Unsaturated aldehydes generated by tertiary ami
