Novel Copper Catalysts for C-H bond Amination and Olefin Aziridination
Section: For Industry
Category(ies): Chemistry
Reference #: WATI222002
OTC Contact: Dave Odelson, Ph.D. (Directory Information | Send a Message)
Description
The insertion of nitrene (NR) into a C-H bond to form an amine is a transformation with great synthetic promise, yet this methodology is limited by facile means of generating nitrene intermediates with appropriate reactivity and selectivity profiles. The present invention describes a novel copper catalyst designed for C-H bond amination and olefin aziridination. This technology promotes the formation of C-N bonds which occur in many classes of fine chemicals using readily available organic azides N=N=NR, which serve as sources of the nitrene functionality.
Applications
Applications:
- Amination of C-H bonds with organoazides
- Aziridination of alkenes with organoazides
- Environmentally friendly syntheses (nitrogen gas only stoichiometric byproduct)
- Lower cost compared to existing rhodium-based catalysts
- Use of copper in catalyst is favorable for its ready availability, and acceptable reactivity with a wide range of olefins and diazo compounds.
- Can be conducted in aerobic environment.
- Can be extended to use stereoselective and enantiospecific C-H bond aminations and olefin aziridinations.
Advantages
Stage of Development
Stage of Development: Proof of concept studies done.
Relevant Publications
- Cu(I) beta-diketiminates for alkene aziridination: reversible Cu-arene binding and catalytic nitrene transfer from PhI=NTs.; Warrant et al; Inorg Chem. 2004 Oct 18;43(21):6537-9.
- A terminal Ni(III)-imide with diverse reactivity pathways.; Warren et al; J Am Chem Soc. 2005 Aug 17;127(32):11248-9.
- Transient terminal Cu-nitrene intermediates from discrete dicopper nitrenes., Warren et al; J Am Chem Soc. 2006 Nov 29;128(47):15056-7.
Patent Status
PCT application PCT/US07/086506 filed on December 5, 2007.
