54783-54-9Relevant academic research and scientific papers
Silver-catalyzed direct couplings of 2-substituted furans with cyclic 1,3-dicarbonyls
Arcadi, Antonio,Alfonsi, Maria,Marinelli, Fabio
, p. 5322 - 5326 (2007)
Direct alkenylation of 2-substituted furans with cyclic 1,3-dicarbonyls by means of silver catalysis have been explored. Silver salts resulted more efficient than a variety of Lewis acids and p-TsOH.
Palladium-Catalyzed Controllable Reductive/Oxidative Heck Coupling between Cyclic Enones and Thiophenes via C-H Activation
Wen, Zhen-Kang,Zhao, Ze-Kai,Wang, Ning-Jing,Chen, Zi-Ling,Chao, Jian-Bin,Feng, Li-Heng
supporting information, p. 9545 - 9549 (2019/11/28)
Herein, we report a straightforward, environmentally friendly, and controllable palladium/ligand catalytic system to enable reductive/oxidative Heck reactions of cyclic enones with thiophene or furan derivatives via C-H activation. The key to this tunable reaction is the appropriate intercepting thienyl-Pd(II)-enolate during the enolization process. Such a controllable and economic protocol would not only provide efficient methods to construct various value-added β-heteroarylated cyclic ketones/enones but also shed light on developing other conjugate addition reactions via C-H activation.
Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: A rapid access to β-heteroarylated cyclic enones
Wen, Zhen-Kang,Song, Ting-Ting,Liu, Yu-Fang,Chao, Jian-Bin
supporting information, p. 3668 - 3671 (2018/04/12)
Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C-H functionalization under mild reaction conditions is reported. Simple substituted thiophenes with different functional groups can be directly introduced into cyclic enones with predominant regioselectivity at the α position of thiophene moieties and excellent functional group tolerance. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenol derivatives have also been demonstrated.
An easy route to 11-hydroxy-eudesmanolides. Synthesis of (±) decipienin A
Moreno-Dorado, F. Javier,Guerra, Francisco M.,Aladro, F. Javier,Bustamante, Jesus M.,Jorge, Zacarias D.,Massanet, Guillermo M.
, p. 6997 - 7010 (2007/10/03)
The preparation of 11-hydroxy-eudesmanolides with the stereochemistry found in the Umbelliferae family of plants is described. The decalin system of the eudesmane skeleton is produced by the addition of 5-methyl-2- furyllithium to 3-ethoxycyclohex-2-enone and acidic treatment of the resulting adduct. The stereochemistry of the decalones obtained by this method has been corrected. The α-hydroxy-γ-lactone moiety is obtained by condensation of the appropriate decalone with methyl pyruvate and subsequent reduction under Luche conditions. The usefulness of this procedure has been proven in the synthesis of decipienin A.
