Iron-catalyzed intramolecular C-H amination of azides
Overview
Laboratory for Synthetic Chemistry and Chemical Biology Limited (LSCCB) has developed a series of iron complexes that can catalyze intramolecular C-H amination of azides to access a wide range of bioactive N-heterocycles.
Technical name of innovation
New generation of Iron-catalyzed intramolecular C-H amination of azides, Product turnover number (TON) > 10,000.
Commercialisation opportunities
technology licensing agreement
Problem addressed
Nitrogen-containing organic compounds are privileged structural motifs in natural products, pharmaceuticals and fine chemicals but predominant strategies for C-H amination require the use of precious metals such as rhodium and ruthenium. Our newly developed iron compounds effectively aminate C-H bonds with alkyl/aryl azides as the nitrogen source to afford a variety of nitrogen-containing compounds.
Innovation
- New chiral porphyrin ligand systems have been developed.
- C-H amination can be conducted under visible-light irradiation with temperature below 40 degree Celsius.
Key impact
- These iron-catalyzed aminations display high diastereo- and enantioselectivity with a broad substrate scope.
- These reactions can be conducted under thermal condition or visible-light irradiation.
Application
- Late-stage functionalization of active pharmaceutical ingredients (API)
Patent
- US patent Application: 17/821,314
- CN patent Application: 202211011556.1
Laboratory for Synthetic Chemistry and Chemical Biology (LSCCB) is an R&D centre funded by Health@InnoHK progamme of Innovation and Technology Commission of HKSAR. Established in 2020, LSCCB is operated with tripartite joint collaboration of The University of Hong Kong, Imperial College London and Peking University. LSCCB aims at integrating chemical and biomedical sciences to develop new molecular medicines and diagnostic tools for the treatment and analysis of human diseases, in particular, cancer. LSCCB currently assembles more than 20 principal investigators for 4 major research programmes including (a) Synthetic Chemistry; (b) Chemical Biology of Natural Products and Chinese Medicine; (c) Metal Anticancer Medicine, Diagnostics and Theranostics; and (d) Multi-Omics and Innovative Analytical Technologies for InnoHealth.
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