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Synthesis 2021; 53(18): 3361-3371
DOI: 10.1055/a-1401-4486
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
We acknowledge financial support from NSFC (21772208, 22001226, 21633013), Natural Science Foundation of Jiangsu Province (BK20201183), Key Research Program of Frontier Sciences of CAS (QYZDJSSW-SLH051), The Natural Science Foundation of the Jiangsu Higher Education Institutions of China (20KJB150016), and Funding for School-Level Research Projects of Yancheng Institute of Technology (xjr2019032).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1401-4486.
- Supporting Information
Publication History
Received: 07 February 2021
Accepted after revision: 26 February 2021
Accepted Manuscript online:
26 February 2021
Article published online:
29 March 2021
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23 After the formation of the isocyanate intermediate, a possible Pd(II)-catalyzed pathway to afford the final product is also considered (Figure S2 in Supporting Information). The main mechanistic difference for Pd(II)-catalyzed pathway is that the acetate ligand could serve as a proton shuttle to assist the H-migration to yield the final product.