Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 44, Pages 12986-12990Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505192
Keywords
amidation; halogen bonding; iodination; peptide formation; umpolung
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Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Multidimensional Materials Science Leaders Program
- Grants-in-Aid for Scientific Research [15K05493, 14J03546] Funding Source: KAKEN
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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 I-2 and K2CO3 under O-2. Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form -iodo nitroalkanes as precursors to the amides.
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