Diisopropyl azodicarboxylate (DIAD)
A nitroxyl-radical-catalyzed oxidation using diisopropyl azodicarboxylate (DIAD) allows the conversion of various primary and secondary alcohols to their corresponding aldehydes and ketones without overoxidation to carboxylic acids. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.
M. Hayashi, M. Shibuay, Y. Iwabuchi, J. Org. Chem., 2012, 77, 3005-3009.
A photoorganocatalytic reaction of aldehydes with diisopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford amides. This method enables a mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines.
G. N. Papadopoulos, C. G. Kokotos, J. Org. Chem., 2016, 81, 7023-7028.
A modified Larock method enables a one-pot synthesis of substituted quinolines via a Heck reaction of 2-bromoanilines and allylic alcohols followed by dehydrogenation with diisopropyl azodicarboxylate (DIAD).
M. T. Stone, Org. Lett., 2011, 13, 2326-2329.