189102-85-0Relevant articles and documents
A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes
El-Shehawy, Ashraf A.,Abdo, Nabiha I.,El-Barbary, Ahmed A.,Lee, Jae-Suk
, p. 4526 - 4529 (2010)
A straightforward method for the synthesis of 2-bromo-4-alkylthiophenes was developed, and the desired products were obtained in the highest chemical yields (>90%) reported to date. 2-Bromo-4-alkylthiophenes were synthesized by regioselective lithiating of 3-alkylthiophenes with n-BuLi and quenching with bromine at -78°C. Moreover, a simple and efficient protocol for the synthesis of dihexyl-2,2′-bithiophenes was developed by employing 2-bromo-4-hexylthiophene instead of the commonly used monomer, 2-bromo-3-hexylthiophene. Kumada and Suzuki cross-coupling reactions were conducted to synthesize the desired products as head-to-tail (HT) and tail-to-tail (TT) regioisomers in high yields and excellent selectivity.
