1,1-Dibromo-3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene (DBBF) is a practical reagent for perfluoro-tert-butylation reactions with various electrophiles. Previously, this reaction has been performed with very dangerous, toxic reagents such as perfluoroisobutylene (PFIB)1. DBBF offers a simpler procedure and a larger scope of substrates. It is a colorless liquid, and easy to work with. The standard procedure for the reaction is activation by CsF in DMF at ambient temperature and can be successfully scaled to a multigram load1. It is well-suited for a wide variety of structurally diverse substrates bearing different functional groups: phenyl, halogens, nitrile, nitro, acyl, sulfonyl, and esters1. Many heterocycles are tolerated: quinolone, naphthalene, benzothiophene, thiophene, and pyridine1. The reagent can be employed for reactions with biomolecules for probing or modification. Overall, the procedure is remarkably selective and predictable, making this reagent a reliable tool.
Synonyms: 1,1-dibromo-3,3,3-trifluoro-2-(trifluoromethyl)-1-propene; 1,1-dibromo-2,2-bis(trifluoromethyl)ethylene; 1,1-dibromo-3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene; DBBF
Selected publication
Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro‐ Tert ‐butylation with 1,1‐Dibromo‐2,2‐bis(Trifluoromethyl)Ethylene (DBBF) and CsF.
Wang Q.; Tao Q.; Dong H.; Ni C.; Xie X.; Hu J. Angewandte Chemie International Edition 2021, 60 (52), 27318–27323. DOI: 10.1002/anie.202113727
