Figure 1. Scope of NaBH4 mediated hydrodefluorination.

Adaptations of standard conditions were as follows: ^a1:1 v:v THF:DMSO used as solvent, ^bheated to 45 °C, ^c2.2 equiv NaBH₄ used, ^dpure THF used as solvent, ^e3 equiv NaBH4 used, ^fheated to 80 °C, ^gDME used as sole solvent, ^h19F NMR yield determined on crude reaction mixture using fluorobenzene as internal standard. ⁱA 90% yield was afforded for a subsequent 5 g scale synthesis of 1b.