Aromatic‐Amide‐Derived Olefins as a Springboard: Isomerization‐Initiated Palladium‐Catalyzed Hydrogenation of Olefins and Reductive Decarbonylation of Acyl Chlorides with Hydrosilane |
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Authors: | Xing‐Feng Bai Prof?Dr Li‐Wen Xu Long‐Sheng Zheng Dr Jian‐Xiong Jiang Prof Guo‐Qiao Lai Jun‐Yan Shang |
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Institution: | Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012 (P.R. China), Fax: (+86)?571‐28865135 |
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Abstract: | 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 cis–trans 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. |
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Keywords: | alkenes decarbonylation isomerization palladium reduction |
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