Journal
SCIENCE ADVANCES
Volume 3, Issue 8, Pages -Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/sciadv.1700826
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Funding
- Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, the Tsinghua-Peking Center for Life Sciences
- 1000 Talents Recruitment Program
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Although azides have been widely used in nitrene transfer reactions, in situ generation of N-H imines fromazides for downstream transformations has rarely been explored. We report copper- mediated formation of N-unsubstituted aliphatic imines from easily available aliphatic azides using a customized phenanthroline-based ligand (L-1*). Through trapping in situ-generated N-H imines, multisubstituted pyridines or indoles were readily synthesized. C-13-labeled azide was used as part of an isotope labeling study, which suggests that the construction of pyridine derivatives involves a three-component dehydrogenative condensation. The construction of 2,3,5-triaryl pyridines using this method provided evidence supporting a proposed pathway involving both imine formation and abnormal Chichibabin pyridine synthesis. The generation of N-unsubstituted imine intermediates was also confirmed by formation of indole derivatives from alkyl azides.
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