Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Zheng-Yang Gu; Yang Wu; Feng Jin; Xiaoguang Bao; Ji-Bao Xia

doi:10.1055/a-1401-4486

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(18): 3361-3371
DOI: 10.1055/a-1401-4486

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

Zheng-Yang Gu‡

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

^bCollege of Textiles and Clothing & Key Laboratory for Advanced Technology in Environmental Protection of Jiangsu Province, Yancheng Institute of Technology, Yancheng, 224051, P. R. of China

,

Yang Wu‡

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

,

Feng Jin

^cCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. of China

,

Xiaoguang Bao∗

^cCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. of China

,

Ji-Bao Xia ∗

^aState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

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Abstract

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Abstract

An atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Key words

C–H carbonylation - amidation - palladium - alkene - amides

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Referenzen

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Zusatzmaterial

Supporting Information