Description:
Princeton Docket # 18-3374-1
The first and only method for preparing high-valued aliphatic isocyanates via direct C-H activation has been developed by researchers at Princeton University.
Organic isocyanates are versatile intermediates that provide access to a wide range of functionalities found in pharmaceuticals and agrochemicals. This method harnesses the synthetic utility of isocyanates and the ubiquitous C-H bonds in organic molecule to enable more step economical routes to compounds that are difficult to prepare. The reaction proceeds efficiently at room temperature and can be applied to functionalize secondary, tertiary, and benzylic C-H bonds with good yields and functional group compatibility. To demonstrate the synthetic potential of this method, the researchers have shown that isocyanate products can be readily converted to substituted ureas without isolation. This method can be useful toward synthesizing many members of molecular scaffolds used for high throughput testing.
Applications:
• Pharmaceutical and agrochemical compound preparation
• Optimization upon current synthesis routes
• Efficient means to create molecular scaffolds for high throughput screening
Advantages:
• Direct route: efficient & economical
• Room temperature
• Good yield
• Unique methodology
Publication:
Huang, X.; Zhuang, T.; Kates, P.A.; Gao, H.; Chen, X.; Groves, J.T. Alkyl Isocyanates via Manganese-Catalyzed C-H Activation for the Preparation of Substituted Ureas. J. Am. Chem. Soc. 2017, 139, 1547-15413. DOI: 10.1021/jacs.7b07658
The Inventors:
John T. Groves is the Hugh Stott Taylor Chair of Chemistry, Professor of Chemistry. Professor Groves’s major thrust of research is at the interface of organic, inorganic, and biological chemistry. His current efforts focus on the design of new, biomimetic catalysts and the molecular mechanisms of these processes, the design and assembly of large scale membrane-protein-small molecule constructs, studies of host-pathogen interactions related to iron acquisition by small molecule siderophores and molecular probes of the role of peroxynitrite in biological systems. Professor Groves is a member of the National Academy of Sciences and the recipient of many accolades, including American Chemical Society National Award in Inorganic Chemistry (2015), Hans Fischer Career Award in Prophyrin Chemistry (2010), and the Remsen Award (2010). He also was one of two people selected to receive the 2008 Grand Prix de la Fondation de la Maison de la Chimie, for his work with cytochrome P450 enzymes and model metalloporphyrin catalysts.
Xiongyi Huang was a graduate research assistant in the Groves group.
Thompson Zhuang was an undergraduate research assistant in the Groves group.
Intellectual Property Status:
Patent protection is pending.
Princeton is seeking to identify appropriate partners for the further development and commercialization of this technology.
Contacts:
Laurie Tzodikov
Princeton University Office of Technology Licensing • (609) 258-7256• tzodikov@princeton.edu
Linda Jan
Princeton University Office of Technology Licensing • (609) 258-5579• ljan@princeton.edu