5923-10-4Relevant academic research and scientific papers
Methylation Alkynylation of Terminal Alkenes via 1,2-Alkynyl Migration Using Dicumyl Peroxide as the Methyl Source
Qin, Yi-Qun,Chen, De,Liu, Liang,Zhang, Jia-Jia,Peng, Xin-Ju,Luo, Yong-Yue,Deng, Wei,Xiang, Jiannan
, p. 4700 - 4708 (2021/08/31)
The metal-free oxidative alkene methylation/alkynylation of 1,4-enyn-3-ols with an organic peroxide as the methyl source has been developed, which provides straightforward and practical access to the challenging quaternary-carbon-containing but-3-yn-1-one
General Synthesis of α-Alkyl Ynones from Morpholine Amides and 1-Copper(I) Alkynes Promoted by Triflic Anhydride
Weng, Yunxiang,Min, Lin,Zeng, Xiaobao,Shan, Lidong,Wang, Xinyan,Hu, Yuefei
supporting information, p. 8296 - 8301 (2020/11/03)
The first general method for the synthesis of α-alkyl ynones was developed based on the strategy of electrophilic activation of amides. Its distinctive advantages are attributed to the use of air-stable "bare"1-copper(I) alkyne as a mild nucleophile witho
Synthesis of C4-alkynylisoxazoles: Via a Pd-catalyzed Sonogashira cross-coupling reaction
Yang, Wen,Yao, Yongqi,Yang, Xin,Deng, Yingying,Lin, Qifu,Yang, Dingqiao
, p. 8894 - 8904 (2019/03/28)
A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The result
Lewis-base-catalysed selective reductions of ynones with a mild hydride donor
Sch?mberg,Zi,Vilotijevic
supporting information, p. 3266 - 3269 (2018/04/05)
Ynones are efficiently reduced with a mild hydride donor in the presence of a catalytic amount of nucleophilic phosphines. The reactions are selective 1,2-reductions that give propargyl alcohols in yields of up to 96%. It is proposed that success in these reactions depends on the activation of ynones by a Lewis base catalyst. A protic additive plays a key role in suppressing the undesired reaction pathways and accelerating the 1,2-reductions.
Complementary regioselective synthesis of 3,5-disubstituted isoxazoles from ynones
Liu, Xiaochen,Hong, Dongsub,She, Zhigang,Hersh, William H.,Yoo, Barney,Chen, Yu
, p. 6593 - 6606 (2018/10/05)
Two regioselective synthetic routes towards 3,5-disubstituted isoxazoles from ynones are reported. One route takes place via first converting the ynones to ynone O-methyl oximes, followed by a palladium-catalyzed intramolecular cyclization. The other invo
Alkynylation of Csp2 (O)–H Bonds Enabled by Photoredox-Mediated Hydrogen-Atom Transfer
Mukherjee, Satobhisha,Garza-Sanchez, R. Aleyda,Tlahuext-Aca, Adrian,Glorius, Frank
, p. 14723 - 14726 (2017/10/18)
The development of new hydrogen-atom transfer (HAT) strategies within the framework of photoredox catalysis is highly appealing for its power to activate a desired C?H bond in the substrate leading to its selective functionalization. Reported here is the first photoredox-mediated hydrogen-atom transfer method for the efficient synthesis of ynones, ynamides, and ynoates with high regio- and chemoselectivity by direct functionalization of Csp2 (O)?H bonds. The broad synthetic application of this method has been demonstrated by the selective functionalization of C(O)?H bonds within complex molecular scaffolds.
Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones
Levashov, Andrey S.,Aksenov, Nicolai A.,Aksenova, Inna V.,Konshin, Valeriy V.
, p. 8297 - 8304 (2017/08/14)
The reaction of tetraalkynyltin with aldehydes was studied for the first time. The reaction was shown to proceed as a tandem process of nucleophilic addition of tin acetylide to aldehyde followed by Oppenauer-type oxidation of produced tin alcoholates, an
Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Chromium(0) Fischer Carbene Complexes
Wang, Kang,Wu, Fengjin,Zhang, Yan,Wang, Jianbo
supporting information, p. 2861 - 2864 (2017/06/07)
Alkyl chromium(0) carbene complexes typically undergo cycloadditions with alkynes to afford carbo- or heterocyclic compounds. In the presence of Pd catalyst, it is demonstrated that a traditional cycloaddition pathway is completely altered: instead of cyc
Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis
Zhou, Quan-Quan,Guo, Wei,Ding, Wei,Wu, Xiong,Chen, Xi,Lu, Liang-Qiu,Xiao, Wen-Jing
supporting information, p. 11196 - 11199 (2016/07/06)
Visible-light-induced photocatalytic decarboxylative alkynylations of carboxylic acids have been developed for the first time. The reaction features extremely mild conditions, broad substrate scope, and avoids additional oxidants. Importantly, a decarboxy
