Proprietary Technologies
CSOL Proprietary Technologies
Air and moisture stable anchorable catalyst for “click” chemistry
Air and moisture stable catalytic system for “click” chemistry, operating in benign conditions and low catalyst loadings. This is a highly efficient system offering the possibility to operate under homogeneous and heterogeneous conditions.
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1,2,3-triazoles are scaffold of interest for the pharmaceutical industry since they are found in many bioactive compounds. However, their production usually involves the handling of hazardous azide derivatives. The use of the developed polymer supported catalyst in microflow reactors presented here enables to tackle the safety issues related to the handling of azides at the large production scale.
The catalyst consists in a new readily accessible functionalized tris(1,2,3-triazol-4-yl) derivative. Its copper(I) complex has proven to be highly air and moisture stable and to be an outstanding catalyst for the production of 1,2,3-triazoles out of azides and alkynes derivatives, providing high yields in short reaction times at room temperature. Thanks to its unique structure, the catalyst can be immobilized on a polymer resin so that the resulting heterogeneous catalyst can be recycled without significant loss of activity.
The catalyst performs at low loadings and in water or under neat conditions and is compatible with a wide range of functional groups, most outstandingly with free amino groups, which makes it ideal for applications in biosciences and for the synthesis of biologically relevant molecules. To the best of our knowledge, this is the best catalyst for copper-catalyzed alkyne-azide cycloaddition reaction in terms of activity, reaction conditions and turnover frequency.
Main advantages:
- 1,2,3-triazole derivatives are highly relevant for the pharmaceutical industry
- Catalyst is readily available from raw materials
- Catalyst can be easily immobilized and reused without loss of efficiency
- Highly efficient and stable catalytic system
- High tolerance to the presence of functional groups on the substrates of the reaction
- Operates in environmentally friendly conditions
- Fast and clean reaction
- Easy product purification (filtration)
References
Pericàs et al. Org. Lett. 2009, 11, 4680-4683