97853-38-8Relevant academic research and scientific papers
Copper-catalyzed trifluoromethylation of internal olefinic C-H bonds: Efficient routes to trifluoromethylated tetrasubstituted olefins and N-heterocycles
Mao, Zhifeng,Huang, Fei,Yu, Haifeng,Chen, Jiping,Yu, Zhengkun,Xu, Zhaoqing
supporting information, p. 3439 - 3445 (2014/04/03)
The functionalization of internal olefins has been a challenging task in organic synthesis. Efficient CuII-catalyzed trifluoromethylation of internal olefins, that is, α-oxoketene dithioacetals, has been achieved by using Cu(OH)2 as a catalyst and TMSCF3 as a trifluoromethylating reagent. The push-pull effect from the polarized olefin substrates facilitates the internal olefinic C-H trifluoromethylation. Cyclic and acyclic dithioalkyl α-oxoketene acetals were used as the substrates and various substituents were tolerated. The internal olefinic C-H bond cleavage was not involved in the rate-determining step, and a mechanism that involves radicals is proposed based on a TEMPO-quenching experiment of the trifluoromethylation reaction. Further derivatization of the resultant CF 3 olefins led to multifunctionalized tetrasubstituted CF3 olefins and trifluoromethylated N-heterocycles.
Palladium-catalyzed oxidative heck-type allylation of β,β- disubstituted enones with allyl carbonates
Jin, Weiwei,Yang, Qin,Wu, Ping,Chen, Jiping,Yu, Zhengkun
supporting information, p. 2097 - 2102 (2014/07/07)
The palladium-catalyzed oxidative Heck-type allylation of β,β-disubstituted enones, i.e., α-oxoketene dithioacetals, was efficiently realized with allyl carbonates, providing a concise route to highly functionalized dienes. The present synthetic methodology utilizes the substrate activation strategy to activate the C-H bond of β,β-disubstituted enones by introduction of a 1,2-dithiolane functionality to make the enone substrate highly polarized and thus increase its reactivity, demonstrating rare examples for transition metal-catalyzed allylic substitution of ss,ss-disubstituted enones through a Heck-type allylation process.
α-alkenoyl ketene S,S-acetal-based multicomponent reaction: An efficient approach for the selective construction of polyfunctionalized cyclohexanones
Ma, Yuhui,Wang, Mang,Li, Dan,Bekturhun, Bahargul,Liu, Jun,Liu, Qun
supporting information; experimental part, p. 3116 - 3121 (2009/08/15)
A versatile multicomponent reaction based on the new four-carbon synthons α-alkenoyl ketene S,S- acetals 1 has been developed. This three-component reaction of readily available α-alkenoyl ketene S,S- acetals 1 with aldehydes 2 and active methylene compou
Dimsyl anion mediated tandem fragmentation cyclization reactions of alkenoyl ketenedithioacetals: A facile synthesis of substituted 2,3-Dihydro-4H-thiopyran-4-ones
Samuel,Nair,Asokan
, p. 1804 - 1806 (2007/10/03)
Dimsyl sodium induced anionic ring cleavage of 1-(1,3-dithiolane-2-ylidene)-4-aryl-3-butene-2-ones followed by intramolecular cyclisation of the intermediate thiolate anion gave 2-aryl, 6-(vinylsulfanyl)-2,3-dihydro-4H-thiopyran-4-ones in good yields.
A novel route to alkenoyl- and cinnamoylketene dithioacetals
Choi,Youn,Pak
, p. 15 - 18 (2007/10/02)
2-Acetyl(ethoxycarbonyl)methylene-1,3-dithietane and -dithiane (1) were condensed with various aldehydes or ketones to afford high yields of the corresponding substituted 2-(1-carboxy-2-oxo-3-butenylidene)-1,3-dithietanes and -dithianes 4, which upon heating decarboxylated smoothly to give the title compounds in high yield.
