2876-78-0Relevant articles and documents
Palladium-catalyzed cascade synthesis of spirocyclic oxindoles via regioselective C2-H arylation and C8-H alkylation of naphthalene ring
Luo, Xiai,Li, Wenguang,Lu, Haiyan,Deng, Guobo,Yang, Yuan,Yang, Chunming,Liang, Yun
, p. 713 - 716 (2021)
A simultaneous C2-H arylation and C8-H alkylation of naphthalene ring has been achieved by palladium-catalyzed cascade reaction of N-(2-halophenyl)-2-(naphthalen-1-yl)acrylamides with aryl iodides, which provides an efficient method for synthesizing various aryl-substituted spirocyclic oxindoles. The protocol enables three C–C bonds formation via an intramolecular Heck reaction and sequentially regioselective C–H bond activation.
Synthesis of 9,10-bis(trifluoromethyl)benzobarrelenes through reaction of hexafluorobut-2-yne and substituted naphthalenes
Kremlev, Mikhail M.,Mushta, Oleksii I.,Yagupolskii, Yurii L.,Rusanova, Julia A.,Peng, Sheng,Petrov, Viacheslav
, (2020)
The cycloadducts 9,10-bis(trifluoromethyl)benzobarrelenes were prepared by the reaction of hexafluorobut-2-yne (HFB) with 1- and, 2- substituted naphthalenes in moderate to high yields. In most cases the reaction proceeds with the formation of two isomeric products derived from cycloaddition of HFB to different aromatic rings of the naphthalene system. The individual isomers were isolated by column chromatography and fully characterized. The basic hydrolysis of ester derivatives of the various 9,10-bis(trifluoromethyl)benzobarrelenes provided the corresponding acids.
Spectroscopic, microscopic and first rheological investigations in charge-transfer interaction induced organogels
Das, Rajat K.,Banerjee, Supratim,Raffy, Guillaume,Del Guerzo, Andre,Desvergne, Jean-Pierre,Maitra, Uday
, p. 7227 - 7235 (2010)
This article describes two-component charge-transfer interaction mediated organogels (CT-gels) derived from anthracene carboxamides obtained from 2-amino-2-hydroxymethyl-1,3-propanediol (TRIS), and 2,3-dialkoxyanthracenes as donors, with 2,4,7-trinitrofluorenone (TNF) as the common acceptor. We demonstrate the versatility of TNF as an electron acceptor in the formation of these gels. The effect of subtle changes in the donor structure on the gelation ability has been investigated by varying the alkyl chain length in the dialkoxyanthracene donors, and by varying the position of the TRIS substituent in the anthracene carboxamide donors. Distinct differences have been observed in the nature of the CT-gels based on these two kinds of anthracene donors. It has been reported in the literature that 2,3-dialkoxyanthracenes form gels on their own in various aliphatic hydrocarbons and alcohols for linear alkyl chains bearing at least 6 carbon atoms (C6). In the present study, it is shown that the CT-complex of these molecules with TNF is able to gel many alcoholic and a few hydrocarbon solvents. Also, in the presence of TNF, the 2,3-dialkoxyanthracenes (C4-C5) which were non-gelators on their own at ambient temperatures, form CT-gels in a number of alcohols. The other series of gelators discussed, the anthracene carboxamides, require the mandatory presence of TNF to form gels. This donor-acceptor complex forms gels in various aliphatic alcohols. Interestingly, the formation of these CT-gels requires rapid cooling in most of the cases. Thermal stability studies with both types of CT-gels indicate an optimum stoichiometry of 1:1 between the donor and the acceptor. Dynamic rheological experiments reveal these gels as viscoelastic soft materials, with the mechanical strength of these gels depending on the amount of TNF present. This provides a means to tune the strength of the gel by varying the doping concentration of the acceptor.
Photoredox-Catalyzed Ring-Opening Addition Reaction between Benzyl Bromides and Cyclic Ethers
Gu, Yucheng,Hu, Jinbo,Kuang, Cuiwen,Ni, Chuanfa
, (2021/12/24)
A novel nucleophilic reaction between cyclic ethers and benzyl bromides is achieved under photoredox catalysis. The reaction proceeds through a single-electron-transfer (SET) pathway rather than a common SN2 mechanism. By two steps of reduction and oxidation, a benzyl bromide heterolyzes to give a carbocation and bromide ion under mild conditions, and then a cyclic ether captures both the carbocation and bromide ion to afford the addition product.
Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite
Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao
supporting information, p. 2713 - 2718 (2021/06/25)
In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.
