Synthesis of 4-Substituted Dibenzothiophenes from Dibenzothiophene-5-Oxide
Hu, Xiaofang, et al. Organic & Biomolecular Chemistry, 2023, 21(46), 9123-9127.
The synthesis of 4-substituted dibenzothiophenes (DBT) from dibenzothiophene-5-oxide (DBTO) can be achieved using a one-pot method. The method involves a sulfoxide-guided C-H metallation/boration/B2Pin2-mediated reduction/Suzuki coupling process. A variety of DBT-based heterobiaryl compounds were successfully prepared using DBTO as a model substrate.
Synthesis of DBT compounds from DBTO
· Optimal reaction conditions: DBTO (0.2 mmol), LiHMDS base (6.0 eq.), B2Pin2 (5.0 eq.), THF (1.2 mL), at 55 °C under Ar atmosphere for 13 h.
· Aryl halides with electron-withdrawing groups (including NO2, aldehydes, and ketones) at the ortho, meta, and para positions afforded the corresponding Suzuki coupling products in 35% to 76% yield.
· 1-tert-butyl-4-iodobenzene and 2-iodoanisole were also successfully converted into 4-aryl-substituted DBT products, with yields of 79% and 54%, respectively.
· The luminescent material PhImPOTD 39 was successfully synthesized through the reaction of DBTO and PhImPOI through a one-pot two-step method with a yield of 62%.