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A little bit of boron takes scientists a long way

EU-funded scientists dramatically increased the building blocks available to synthetic chemists. The result is novel fluorescent compounds for biological sensors and a thermometer.
A little bit of boron takes scientists a long way
Industrial synthetic chemistry relies on a store of ligands and highly selective catalysts that can be used to produce a variety of fine chemicals of interest. Thus, a key driver of research is the development of novel ligands and catalysts for known reactions that are currently lacking suitable compounds or for new reactions that would lead to novel products.

Scientists initiated the EU-funded project 'Applications of new chiral nitrogen-based ligands in asymmetric catalysis' (ANCNAC) to develop a novel family of nitrogen-based ligands (nitrogen donors) as an alternative to phosphorous-based ones for access to new organic compounds. Due to the lack of reactivity or enantioselectivity in the planned Palladium (Pd), Copper (Cu) catalyzed reactions in the first few months of the project, led the team to redirect it and to focus on borylation of carbon–hydrogen (C-H) bonds employing nitrogenated ligands.

Investigators had great success with C-H bond borylation experiments. Conversion of unreactive C-H bonds to C–Boron (B) ones enabled the synthesis of many intermediates for the synthesis of value-added fine chemicals, including biologically important molecules. Researchers demonstrated complete regioselectivity (selectivity for a specific isomer of a compound) using easy synthesizable and therefore available ligands. Results were extended to a diborylation-process, to synthetize diborylated products which can be used as intermediates for the introduction of two different electrophiles (literally, electron lovers) to give non-symmetric 2,6-disubstituted molecules.

The line of research also led investigators to employ this C-H bond borylation methodology for the synthesis of borylated fluorescent dyes. The novel family of molecular fluorophores were shown to be electronically tuneable and switchable fluorescence emission was also observed. Currently, the team is developing some new systems such as a fluorescent thermometer and sensors for living systems: a hydrogen peroxide (H202) sensor and a carbohydrate sensor.

ANCNAC investigations of borylation and diborylation reactions led to fruitful discoveries important to synthetic chemistry and even to biomedicine. Outcomes are expected to spur the manufacture of novel added-value fine chemicals and their applications, enhancing the competitive position of the EU chemical manufacturing industry and strengthening the EU economy.

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