Categories: C=O Bond Formation >
Synthesis of aldehydes
Reactions
Oxidation of alcohols, rearrangements
Recent Literature

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.
