Categories: C=O Bond Formation > Synthesis of aldehydes >
Synthesis of aldehydes by oxidation of alkenes
Name Reactions
Recent Literature
Osmium tetroxide has been microencapsulated in a polyurea matrix. These
microcapsules have been effectively used as recyclable catalysts in the
dihydroxylation and the oxidative cleavage of olefins.
S. V. Ley, C. Ramarao, A.-L. Lee, N. Ostergaard, S. C. Smith, I. M. Shirley,
Org. Lett., 2003, 5, 185-187.
A gold(I)-catalyzed oxidative cleavage of alkenes with tert-butyl
hydrogenperoxide (TBHP) as the oxidant in the presence of neocuproine
afforded ketones or aldehydes as products.
D. Xing, B. Guan, G. Cai, Z. Fang, L. Yang, Z. Shi, Org. Lett.,
2006, 8, 693-696.
A series of symmetrical and unsymmetrical stilbenes bearing electron-withdrawing
groups were oxidatively cleaved to the corresponding aldehydes in high yield by
electrocatalytic anodic oxidation employing a high oxidation potential
triphenylamine electrocatalyst. The oxidations apparently involve the
corresponding 1,2-diols, which are also converted to aldehydes in high yield
under the same conditions.
X. Wu, A. P. Davis, A. J. Fry, Org. Lett., 2007,
9, 5633-5636.
A catalytic amount of a composite material, RuO2/BaTi4O9,
in combination with NaIO4 in EtOAc-H2O has been shown to
efficiently cleave alkenes, affording ketones, aldehydes and/or carboxylic acids
in high yields.
H. Okumoto, K. Ohtsuko, S. Banjoya, Synlett, 2007,
3201-3205.
Specific oxidation protocols have been developed for the cleavage of styrenes,
aliphatic olefins, and terminal aliphatic olefins to carbonyl compounds with
ruthenium trichloride as catalyst. Olefins that are not fully substituted are
converted to aldehydes rather than carboxylic acids.
D. Yang, C. Zhang, J. Org. Chem., 2001, 66, 4814-4818.
