Late stage functionalisation (LSF) and diversification of advanced lead molecules is a powerful tool for the development of pharmaceutical and other biologically active compounds. This process facilitates investigations into the relationships between the structure of a compound and its activity, the optimization of the biological properties of a compound and the ability to access new intellectual property (IP) space. Often, late stage functionalisation approaches are limited to specific reactions or a narrow set of substrates, and demonstrate poor yields and selectivity when functionalizing more complex compounds. Furthermore, these processes often require harsh reaction conditions, which can lead to significant decomposition and present challenges during the commercialisation and scale up of a process.
This technology is a new generation of ruthenium catalysts capable of vastly outperforming current catalysts on a variety of C-H arylation and alkylation reactions. These new catalysts are so reactive that C-H arylation and alkylation can be performed at close to room temperature, which is significantly lower than the temperatures required by previous state-of-the-art catalysts. Furthermore, because of the high reactivity and efficiency that these novel catalysts demonstrate, they can be used to C-H arylate and/or alkylate complex molecules containing larger and more diverse numbers of functional groups than other competing catalysts. This technology therefore facilitates the direct functionalisation of complex drug molecules and agrochemicals in high yields and chemoselectivity for the first time. As such, this technology represents a powerful and exciting tool for the functionalisation and diversification of biologically and chemically relevant molecules which could be of significant interest to the pharmaceutical and agrochemical industry.
Ruthenium Catalysts for Late Stage Functionalisation
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- The technology is capable of C-H arylating/alkylating molecules containing N- directing groups with coupling partners through C-Cl, C-Br, C-I and C-OH bonds.
- These catalysts work at near room temperature.
- High reactivity and efficiency facilitates chemoselective functionalization of complex molecules in high yields.
- Extremely broad functional group compatibility: eg amines, carbamates, sulfonylureas, alkenes, alcohols, acetals, thiohemiaminals, amidines, anilines, aldehydes, amides, esters, ketones, carboxylic acids, and a variety of N, O, and S containing heterocycles, such as piperidine, pyridine, azepane, indole, carbazole, phenothiazine, β-lactam, sugars and dihydrodibenzoazepine, among many others.
- Late stage functionalization of bio-active compounds in order to improve and optimize absorption, distribution, metabolism and excretion (ADME) properties.
- Facilitation of investigations into structure-activity relationships (SAR) of a target compound without the need for de novo synthesis of each variant.
- A means to access novel IP space from potentially complex drug compounds.
- The development of novel compounds for use in agrochemical or organic electronics industries.
- Lower cost and toxicity compared with Pd-cross coupling processes.
See Nature Chemistry, 2018, 10, 724-731 for other arylation examples.
Two patent applications filed covering catalysts for arylation and alkylation.
Opportunities for potential partnerships related to research and development and/or licensing are available.
UMIP reference numbers 20170183 and 20180064.
Professor Igor Larrosa, School of Chemistry, The University of Manchester, M13 9PL
Allan Prits, Head of Marketing, UMIP, Core Technology Facility, 46 Grafton Street,Manchester, M13 9NT