Photocatalyzed cascade hydrogen atom transfer for the construction of α-CF3-1,4-diketones†

Abstract

The development of novel fluorinated building blocks establishes a crucial basis for the synthesis of fluorinated compounds. CF₃-containing 1,4-diketones could be a new class of fluorinated synthons. Here we report the first synthesis of α-CF₃-1,4-diketones from commercially available aldehydes and 2-bromo-3,3,3-trifluoro-1-propene (BTP) by a cascade hydrogen atom transfer (HAT) process employing tetrabutylammonium decatungstate (TBADT) as a photocatalyst. Notably, this cascade HAT methodology effectively circumvents the common issue of defluorination that typically occurs in previously reported systems. Additionally, the newly synthesized α-CF₃-1,4-diketones could be applied as starting materials for the construction of CF₃-containing heterocycles, thereby expanding the prospects for developing novel pharmaceuticals.