Categories: C=O Bond Formation >
Synthesis of aldehydes
A hypervalent iodine reagent, (diacetoxyiodo)benzene, and catalytic amount of sodium azide in acetonitrile enable an oxidative decarboxylation of 2-aryl carboxylic acids into the corresponding aldehydes, ketones, and nitriles in good yields at room temperature. The advantages of this protocol are short reaction times and mild reaction conditions.
V. N. Telvekar, K. A. Sasane, Synlett, 2010, 2778-2779.
Chromium(III) tetraphenylporphyrin triflate is an efficient and characteristic Lewis acid catalyst for a regio- and stereoselective rearrangement of epoxides to aldehydes. Optically active β-siloxy aldehydes are easily available through Sharpless epoxidation of allylic alcohols, followed by silylation and rearrangement.
K. Suda, T. Kikkawa, S.-i. Nakajima, T. Takanami, J. Am. Chem. Soc., 2004, 126, 9554-9555.
The use of visible-light-induced silver catalysis enables a controlled singlet-oxygen-mediated selective C-S bond cleavage reaction of benzyl thiols to afford carbonyl compounds.
B. Hong, K. C. C. Aganda, A. Lee, Org. Lett., 2020, 22, 4395–4399.
A commercial cyclopentadienylrutenium dicarbonyl dimer efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light.
J. Min Lee, D. Y. Bae, J. Y. Park, H. Y. Jo, E. Lee, Y. H. Rhee, J. Park, Org. Lett., 2020, 22, 4608-4613.