30858-18-5Relevant articles and documents
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
, p. 9545 - 9549 (2019)
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.
