1122594-14-2Relevant academic research and scientific papers
Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach
Tanaka, Ibuki,Sawamura, Masaya,Shimizu, Yohei
supporting information, p. 520 - 524 (2022/01/20)
Reductive alkynylation of aldehydes by the Umpolung approach was developed using a photoredox catalyst under blue LED irradiation. Ketyl radicals, generated by single-electron reduction of aldehydes through proton-coupled electron transfer (PCET), reacted with electrophilic alkynylsulfones. Sterically demanding bulky aldehydes reacted smoothly under the Umpolung reaction conditions. Moreover, the alkynylation proceeded chemoselectively with an aryl aldehyde group in the presence of other carbonyl groups including an aliphatic aldehyde group.
Propargylation of CoQ0 through the Redox Chain Reaction
Mlynarski, Jacek,Pawlowski, Robert,Stodulski, MacIej
, (2022/01/04)
An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.
Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones
Feng, Xiaoming,Liu, Xiaohua,Zeng, Zi,Zhao, Peng
supporting information, p. 132 - 135 (2020/12/21)
The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
supporting information, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand
Zheng, Yin,Qin, Tianzhu,Zi, Weiwei
supporting information, p. 1038 - 1045 (2021/01/25)
Cycloaddition reactions between oxyallyl cations and alkenes are important transformations for the construction of ring systems. Although (4 + 3) cycloaddition reactions of oxyallyl cations are well-developed, (3 + 2) cycloadditions remain rare, and an as
New α-Hydroxy-1,2,3-triazoles and 9H-Fluorenes-1,2,3-triazoles: H Synthesis and Evaluation as Glycine Transporter 1 Inhibitors
Buarque, Camilla D.,Guimar?es, Marilia Z.,López?Corcuera, Beatriz,Neto, Jo?o Gon?alves,No?l, Fran?ois,Silva, Rafaela R.,da Silva, Veronica D.
, p. 1258 - 1269 (2020/10/14)
Two series of new compounds containing 1,2,3-triazole moiety were designed as putative GlyT1 inhibitors aiming the discovery of new hits with activity in cognitive disorders. 1,4-Disubstituted α-hydroxy-1,2,3-triazoles were obtained as racemates in moderate to good yields by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click chemistry) as the key step between propargyl alcohols and aryl azides, previously prepared from anilines or boronic acids. Benzo[c]chromene-triazoles were planned to be obtained by palladium-catalyzed C?H activation using [bis(trifluoroacetoxy)iodobenzene] (PhI(TFA)2) of some α-hydroxy-1,2,3-triazoles, since benzo[c]chromenes are also privileged groups with several biological activities, including to the central nervous system. Unexpectedly, 9H-fluorenes-1,2,3-triazoles, instead of benzo[c]chromenetriazoles, were obtained by Friedel-Crafts alkylation reaction. The two series of compounds were tested for inhibition of the glycine transporter (rat GlyT1 isoform) but only the α-hydroxy-1,2,3-triazole 9b was active (half maximal inhibitory concentration (IC50) = 8.0 μM).
Gold-Catalyzed Dehydrogenative Cycloisomerization of 1,4-Enyne Esters to 3,5-Disubstituted Phenol Derivatives
Chen, Cuili,Chen, Xianxiao,Zhang, Xiaoxiang,Wang, Shifa,Rao, Weidong,Chan, Philip Wai Hong
supporting information, p. 4359 - 4368 (2017/12/26)
A method to prepare synthetically important 3,5-disubstituted phenol derivatives that relies on the sequential gold(I)-catalyzed dehydrogenative cycloisomerization of 1,4-enyne esters in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) or N-fluorobenzenesulfonimide (NFSI) is described. The synthetic versatility of the methodology was exemplified by a gram-scale reaction of one example, the ease to realize subsequent functional transformations of an adduct, and the application of the method to the synthesis of the bioactive molecule LUF5771. (Figure presented.).
Trialkyl Methanetricarboxylate as Dialkyl Malonate Surrogate in Copper-Catalyzed Enantioselective Propargylic Substitution
Huang, Guanxin,Cheng, Cang,Ge, Luo,Guo, Beibei,Zhao, Long,Wu, Xiaoyu
supporting information, p. 4894 - 4897 (2015/10/12)
The first copper-catalyzed enantioselective propargylation of trialkyl methantricarboxylate with propargylic alcohol derivatives was developed. The tricarboxylate unit in the obtained adducts could be easily transformed into a malonate moiety by treating with in situ generated NaOEt in excellent yield without racemization.
Cyclopropanation of strained alkenes by palladium-catalyzed reaction of 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetates
Horino, Yoshikazu,Homura, Naoki,Inoue, Kana,Yoshikawa, Saori
supporting information; experimental part, p. 828 - 834 (2012/05/04)
The palladium-catalyzed cyclopropanation of strained alkenes with 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetate derivatives is described. This reaction gives cyclopropanation products in good to high yields with a single diastereomer, and the key step is likely to involve the formation of a palladacyclobutene complex from the α-trimethylsilyl- or α-pinacolatoboryl-σ-allylpalladium complex. Copyright
Synthesis of allenes via gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds
Xu, Cheng-Fu,Xu, Mei,Yang, Liu-Qing,Li, Chuan-Ying
experimental part, p. 3010 - 3016 (2012/05/05)
Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.
