Unprecedented Demonstration of Regioselective SEAr Reaction giving Unsymmetrical Regioregular Oligothiophenes

作者:Moussallem Chady; Olivier Simon; Grolleau Jeremie; Allain Magali; Mallet Charlotte; Savitha Gurunathan; Gohier Frederic*; Frere Pierre*
来源:Chemistry - A European Journal, 2016, 22(19): 6510-6514.
DOI:10.1002/chem.201600159

摘要

Aromatization of 4-cyano-3-oxotetrahydrothiophene by sulfuryl chloride gives the new building block 4-cyano-3-pyrrolidylthiophene, which forms unsymmetrical regioregular oligothiophenes with a strict alternation of the donor and acceptor groups along the conjugated system. The self-coupling reactions that form the oligomers are shown to proceed by a regioselective electrophilic aromatic substitution mechanism involving a stabilized Wheland intermediate.

  • 出版日期2016-5-4