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Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole
Dominic Taylor1, Thomas Malcomson2, Adilet Zhakeyev3
1Institute of Chemical Sciences, School of Engineering and Physical Science, Heriot-Watt University Riccarton Edinburgh EH14 4AS UK f.vilela@hw.ac.uk.
Abstract:
Regioselective stepwise phenylation of 4,7-diarylbenzo[c][1,2,5]thiadiazole fluorophores has been achieved through a facile one-pot, three-step synthetic strategy involving sequential borylation, hydroxydechlorination and Suzuki-Miyaura cross-coupling reactions. Crucial to the selectivity was the use of BCl3 to regioselectively install a boronic acid group in the ortho-position of only one of the diaryl groups. The subsequent introduction of ortho-phenyl groups through Suzuki-Miyaura cross-coupling gave rise to twisted structures with hindered intramolecular rotation, providing a structural lever with which the fluorophore absorption and emission properties could be adjusted.
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