Summary of the technology
- clean production of trifluromethylcopper reagent
- process works at room temperature and atmospheric pressure
- inexpensive and abundant trifluoromethyl source
- environmentally friendly process
- low-cost reagents
- valorization of fluoroform: a by-product of PTFE production
- Versatile reagent allowing for a broad scope of reactivity
Description of the technology
Chemical compounds bearing a trifluoromethyl group (CF3) are widely used in the production of various pharmaceuticals and agrochemicals as well as specialty materials, polymers, composites, building blocks, and intermediates for various needs. However, the current manufacturing of trifluoromethylated compounds still needs improvements. Trifluoromethyl copper (I) compounds that are particularly useful in various trifluoromethylation reactions of organic molecules are conventionally made using costly CF3 sources. Fluoroform, CF3H, is an ideal source of CF3 because it is inexpensive, readily available in large industrial quantities, non-toxic, and not an ozone depleter. However, the few known methods to prepare trifluoromethyl copper (I) compounds from fluoroform are all not only multistep and low-yielding, but also require low temperatures (-10 - -50 ºC) to minimize the extremely facile decomposition of the highly unstable trifluoromethyl anion that is generated in the first, CF3H deprotonation step. Technology is offered for partnership and licensing; partnership is sought for process optimization and adaptation to specific needs.
The ICIQ technology does not involve deprotonation of CF3H. Instead, the CuCF3 reagents are formed via direct cupration that is not mediated by the unstable trifluoromethyl anion and/or difluorocarbene. As a result, our CuCF3 synthesis proceeds cleanly at room temperature while avoiding the formation of side-products. The trifluoromethyl copper reagents are obtained in high yield of up to >90% and can be used directly in various reactions, including aromatic trifluoromethylation. Treatment of a copper(I) source with 2 equivalents of an alkali metal alkoxide results in the formation of highly reactive dialkoxycuprates that directly metalate fluoroform to give CuCF3 compounds in one step. These CuCF3 reagents can then be used in various reactions with electrophiles to give trifluoromethylated products, including trifluoromethylated aromatic and heterocyclic derivatives.
Main advantages of its use
- crop protection
- fluorine chemistry
- new active ingredients
- performance materials
- waste valorization
Additional information (attached documents)
Intellectual property status
Additional information (attached documents)
About Institute of Chemical Research of Catalonia
Technology Transfer Office from SpainInstitute of Chemical Research of Catalonia
The Institute of Chemical Research of Catalonia represents one of the very first fruits of the new scientific policy of the government of Catalonia (Spain) aimed at creating new research centres in strategic areas. ICIQ, in particular, has been created with the ambition of becoming a reference for chemistry in the European Research Space. Our society faces important challenges in the XXI century, among which health and environmental concerns are of outmost importance. Chemistry will play an essential role in both of these challenges. To succeed, our increasingly knowledge-based economy will require a solid and strong chemical industry; currently 150.000 jobs in Catalonia (and more than 2 million in the EU) directly arise from the chemical industry. In order for this industry to be successful in the future, it must take a sustainable approach based on the rational use of feed-stocks and raw materials. For this, fundamental chemical research needs to be funded and novel approaches into transforming matter must be developed. We at ICIQ consider that catalysis is the key activity for sustainable chemistry. Catalytic processes can minimize raw materials and energy consumption, and can lead to the selective formation of target products with minimal generation of wastes. In line with this consideration, we have taken catalysis as one of our main research topics. Complementary to our research focus, attention has been paid to the development of a simple and efficient organizational model for ICIQ, able to overcome known difficulties normally associated with larger and more traditional research institutions. The Institute of Chemical Research of Catalonia aims at bridging the gap between academic research and industry, focusing its research on catalytic chemical processes for applications in health, energy and sustainability. At ICIQ, we consider that patents are highly efficient, safe and solid tools to provide protection from competitors. This is why we file patents for our in-house developed-technologies: to give our co-development projects with industry a strong starting IP position. As a research centre our goal is always to co-develop our technology adapting it to the industrial partner’s specific needs and ultimately transfer the technology to this company, with a flexible licensing strategy adapted to each case.