Aromatic-Amide-Derived Olefins as a Springboard: Isomerization-Initiated Palladium-Catalyzed Hydrogenation of Olefins and Reductive Decarbonylation of Acyl Chlorides with Hydrosilane

作者：Bai Xing Feng; Xu Li Wen^*; Zheng Long Sheng; Jiang Jian Xiong; Lai Guo Qiao; Shang Jun Yan

来源：Chemistry - A European Journal, 2012, 18(26): 8174-8179.

DOI：10.1002/chem.201200039

• alkenes
• decarbonylation
• isomerization
• palladium
• reduction

A highly efficient catalytic protocol for the isomerization of substituted amide-derived olefins is presented that successfully uses a hydride palladium catalyst system generated from [PdCl2(PPh3)2] and HSi(OEt)3. The Z to E isomerization was carried out smoothly and resulted in geometrically pure substituted olefins. Apart from the cistrans isomerization of double bonds, the selective reduction of terminal olefins and activated alkenes was performed with excellent functional group tolerance in the presence of an amide-derived olefin ligand, and the products were obtained in high isolated yields (up to >99?%). Furthermore, the palladium/hydrosilane system was able to promote the reductive decarbonylation of benzoyl chloride when a (Z)-olefin with an aromatic amide moiety was used as a ligand.

• 出版日期2012-6
• 单位杭州师范大学