Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine |
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| Authors: | Jing Li Prof?Dr Martin J Lear Yuya Kawamoto Dr Shigenobu Umemiya Alice R Wong Prof?Dr Eunsang Kwon Prof?Dr Itaru Sato Prof?Dr Yujiro Hayashi |
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| Institution: | 1. Department of Chemistry, Graduate School of Science, Tohoku University, 6‐3 Aramaki‐Aza, Aoba‐ku, Sendai 980‐8578 (Japan) http://www.ykbsc.chem.tohoku.ac.jp;2. Present address: School of Chemistry, University of Lincoln, Brayford Pool, Lincoln LN6 7TS (UK);3. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980‐8578 (Japan);4. Present address: Faculty of Science, Ibaraki University, Ibaraki 310‐8512 (Japan) |
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| Abstract: | The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom‐economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non‐chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen‐bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α‐iodo nitroalkanes as precursors to the amides. |
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| Keywords: | amidation halogen bonding iodination peptide formation umpolung |
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