54669-76-0Relevant academic research and scientific papers
A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals
Goti, Giulio,Melchiorre, Paolo,O?eka, Maksim,Schweitzer-Chaput, Bertrand,Spinnato, Davide
supporting information, p. 9485 - 9490 (2020/04/09)
Reported herein is a visible-light-mediated radical approach to the α-alkylation of ketones. This method exploits the ability of a nucleophilic organocatalyst to generate radicals upon SN2-based activation of alkyl halides and blue light irradiation. The resulting open-shell intermediates are then intercepted by weakly nucleophilic silyl enol ethers, which would be unable to directly attack the alkyl halides through a traditional two-electron path. The mild reaction conditions allowed functionalization of the α position of ketones with functional groups that are not compatible with classical anionic strategies. In addition, the redox-neutral nature of this process makes it compatible with a cinchona-based primary amine catalyst, which was used to develop a rare example of enantioselective organocatalytic radical α-alkylation of ketones.
Br?nsted Acid-Catalyzed Formal [2 + 2 + 1] Annulation for the Modular Synthesis of Tetrahydroindoles and Tetrahydrocyclopenta[ b]pyrroles
Malone, Joshua A.,Toussel, Courtney E.,Fronczek, Frank R.,Kartika, Rendy
supporting information, p. 3610 - 3614 (2019/05/24)
An expedient synthesis of tetrahydroindoles and tetrahydrocyclopenta[b]pyrroles, highlighted by Br?nsted acid catalyzed formal [2 + 2 + 1] annulation reaction, is reported. Using three readily accessible reaction components, i.e., an electrophilic species in silyloxyallyl cations and two distinct nucleophiles in silylenol ethers and amines, our chemistry enables the assembly and functionalization of these biologically important N-heterocycles in a highly modular manner.
The synthesis of cycloalka[: B] furans via an Au(i)-catalyzed tandem reaction of 3-yne-1,2-diols
Liu, Wei-Ting,Xu, Zheng-Liang,Mou, Xue-Qing,Zhang, Bang-Hong,Bao, Wen,Wang, Shao-Hua,Lee, Dongjun,Lei, Lin-Sheng,Zhang, Kun
supporting information, p. 6333 - 6337 (2017/08/10)
An Au(i)-catalyzed cyclization/1,2-rearrangement/aromatization cascade of 3-yne-1,2-diols has been successfully realized. This reaction not only provides a new and efficient strategy for the synthesis of substituted cycloalka[b]furan compounds as well as their derivatives, but might also facilitate related biological studies.
In order to 2 - halogenated cyclopentanone as raw material for the synthesis of 1, 4 - dione compound method
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Paragraph 0024; 0025; 0026, (2017/08/25)
The invention provides a method for synthesizing 1,4-diketone compound by using 2-halogenated cyclopentanone as a raw material. In the presence of alkali, 2-halogenated cyclopentanone reacts with silyl enol ether in perfluoroalkyl alcohol used as a solven
Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones
Lan, Xing-Wang,Wang, Nai-Xing,Zhang, Wei,Wen, Jia-Long,Bai, Cui-Bing,Xing, Yalan,Li, Yi-He
supporting information, p. 4460 - 4463 (2015/09/28)
A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp3)-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
Catalyst-free formation of 1,4-diketones by addition of silyl enolates to oxyallyl zwitterions in situ generated from α-haloketones
Luo, Juan,Jiang, Qihua,Chen, Hao,Tang, Qiang
, p. 67901 - 67908 (2015/08/24)
Reported here is the exclusive formation of 1,4-diketones by the uncatalyzed reaction of silyl enolates and α-haloketones. Enolates I are inherently more likely to react with α-haloketones II at the carbonyl carbon to produce halohydrin derivatives III or
Synthesis of alkyl aryl ketones by Pd/light induced carbonylative cross-coupling of alkyl iodides and arylboronic acids
Sumino, Shuhei,Ui, Takahito,Ryu, Ilhyong
supporting information, p. 3142 - 3145 (2013/07/26)
Alkyl aryl ketones were synthesized by the carbonylative cross-coupling reaction of alkyl iodides and arylboronic acids under combined Pd/light conditions. In this reaction, it is likely that an acylpalladium species would be formed via carbonylation of t
Oxidative C-C bond cleavage of aldehydes via visible-light photoredox catalysis
Sun, Hongnan,Yang, Chao,Gao, Fei,Li, Zhe,Xia, Wujiong
, p. 624 - 627 (2013/04/23)
The visible-light mediated oxidative C-C bond cleavage of aldehydes has been achieved in good yields at ambient temperature and open to air using Ru(bpy)3Cl2 (bpy = 2,2′-bipyridine) as the photoredox catalyst. Moreover, we further demonstrated the application in a tandem Michael/oxidative C-C bond cleavage reaction.
Enone-alkyne reductive coupling: A versatile entry to substituted pyrroles
Thompson, Benjamin B.,Montgomery, John
, p. 3289 - 3291 (2011/09/13)
The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dica
The cascade carbo-carbonylation of unactivated alkenes catalyzed by an organocatalyst and a transition metal catalyst: A facile approach to γ-diketones and γ-carbonyl aldehydes from arylalkenes under air
Xie, Jin,Huang, Zhi-Zhen
supporting information; experimental part, p. 1947 - 1949 (2010/06/21)
A novel cascade carbo-carbonylation reaction of unactivated arylalkenes with ketones or aldehydes was catalyzed by an organocatalyst and a transition metal catalyst via a SOMO-enamine under air, affording a simple approach to γ-diketones and γ-carbonyl aldehydes. The Royal Society of Chemistry 2010.
