Formation of 2-substituted iodobenzenes from iodobenzene via benzyne and ate complex intermediates

[GRAPHICS] The generation of benzyne from iodobenzene with lithium tetramethylpiperidi de in THF at -40 degrees C in the presence of lithium amides and ester enol ates leads to mixtures in which 2-substituted iodobenzenes are often the ma jor products, These products are obtained by iodine transfer from iodobenze ne to the intermediate 2-lithioaromatics. The transfer of iodine occurs via a hypervalent iodine (ate) complex.