Concise Report
Visible-Light-Mediated Photocatalyst-Free Hydroacylation of Azodicarboxylic Acid Derivatives with 4-Acyl-1,4-dihydropyridines
Li Liu,
Jing Wang,
Xiaoying Feng,
Kun Xu,
Wei Liu,
Xia Peng,
Hongguang Du,
Jiajing Tan,
Li Liu
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Sinopec Beijing Research Institute of Chemical Industry, Beijing, 100013 China
The authors contributed equally.
Search for more papers by this authorJing Wang
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
The authors contributed equally.
Search for more papers by this authorXiaoying Feng
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorKun Xu
Faculty of Environment and Life, Beijing University of Technology, Beijing, 100124 China
Search for more papers by this authorWei Liu
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorXia Peng
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorCorresponding Author
Hongguang Du
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Jiajing Tan
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
E-mail: [email protected]; [email protected]Search for more papers by this authorLi Liu,
Jing Wang,
Xiaoying Feng,
Kun Xu,
Wei Liu,
Xia Peng,
Hongguang Du,
Jiajing Tan,
Li Liu
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Sinopec Beijing Research Institute of Chemical Industry, Beijing, 100013 China
The authors contributed equally.
Search for more papers by this authorJing Wang
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
The authors contributed equally.
Search for more papers by this authorXiaoying Feng
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorKun Xu
Faculty of Environment and Life, Beijing University of Technology, Beijing, 100124 China
Search for more papers by this authorWei Liu
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorXia Peng
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
Search for more papers by this authorCorresponding Author
Hongguang Du
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Jiajing Tan
Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing, 100029 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
A visible-light-enabled, photocatalyst-free hydroacylation reaction of azodicarboxylic acid derivatives was described. This radical conjugate addition (RCA) protocol relied on the dual role of 4-acyl-1,4-dihydropyridine (acyl-DHP) reagents that besides being as radical reservoirs, they also enabled the conversion of radical adducts to anion intermediates via reduction. Under “catalyst-oxidant-additive free” conditions, a wide range of structurally different acyl hydrazide products were readily obtained in 56%—99% yields. The utility of this transformation was further demonstrated by the scale-up synthesis and downstream derivatization.
Supporting Information
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| cjoc202300726-sup-0001-Supinfo.pdfPDF document, 9.1 MB |
Appendix S1: Supporting Information |
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