Scheme 3. Scope of the Decarboxylative Iodination of Benzoic Acids.

Reactions carried out at a 0.5 mmol scale of 1.

Ratios in brackets indicate mono-:diiodinated material by crude GC-FID analysis. Asterisk indicates position of diiodination.

I₂ (3.0 equiv).

NMR yield for reactions employing I₂ (1.0–2.0 equiv), 170 °C and 1,4-dioxane or o-DCB as solvent.

I₂ (6.0 equiv), 140 °C.

I₂ (2.0 equiv).

MeCN (5.0 mL).

I₂ (3.0 equiv), 1,4-dioxane (1.0 M), 170 °C.

Yields determined by quantitative ¹⁹F NMR.

I₂ (2.5 equiv).