Diethyl azodicarboxylate (DEAD)
Mediated by copper/diethyl azodicarboxylate, regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne was successfully established. The alkynylation reaction described here has the advantage of simple operation, mild reaction conditions, good to excellent yields, and no need to exclude air and moisture.
X. Xu, X. Li, Org. Lett., 2009, 11, 1027-1029.
The reaction of aryl diazoacetates with H2O and diethyl azodicarboxylate (DEAD) catalyzed by dirhodium acetate gives aryl α-keto esters in high yields.
Z. Guo, H. Huang, Q. Fu, W. Hu, Synlett, 2006, 2486-2488.
An oxidative C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents is mediated by diethyl azodicarboxylate (DEAD). This C-H activation under metal-free conditions delivers target compounds, including some naturally occurring alkaloids, in good yields.
K. N. Singh, S. V. Kessar, P. Singh, P. Singh, M. Kaur, A. Batra, Synthesis, 2014, 46, 2644-2650.