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: | Bai Xing-Feng Xu Li-Wen Zheng Long-Sheng Jiang Jian-Xiong Lai Guo-Qiao Shang Jun-Yan |
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Institution: | Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, PR China. |
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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 PdCl(2)(PPh(3))(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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