Diisopropyl azodicarboxylate, 94%, Thermo Scientific Chemicals

General References:

1. Alternative to 'DEAD' (Diethyl azodicarboxyl ate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenyl phosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).
2. For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethyl silyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).
3. An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).
4. For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).
5. Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Efficient C-H/C-N and C-H/C-CO-N Conversion via Decatungstate-Photoinduced Alkylation of Diisopropyl Azodicarboxylate. Org. Lett. 2013, 15 (10), 2554-2557.
6. Hayashi, M.; Shibuya, M.; Iwabuchi, Y. Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals. J. Org. Chem. 2012, 76 (6), 3005-3009.