Categories: C=O Bond Formation > Synthesis of aldehydes >
Synthesis of aldehydes by oxidation of alkenes
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Recent Literature
In the presence of PdCl2(MeCN)2, 1,4-benzoquinone, and
t-BuOH, aryl-substituted olefins can selectively be oxidized to aldehydes.
In this efficient and aldehyde-selective Wacker oxidation, very good yield of
aldehyde can be obtained, and up to 99% selectivity can be achieved with
styrene-related substrates.
P. Teo, Z. K. Wickens, G. Dong, R. H. Grubbs, Org. Lett., 2012,
14, 3237-3239.
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.
The use of PhI(OAc)2 in dichloromethane enables a clean oxidative
cleavage of 1,2-diols to aldehydes. In the presence of OsO4 as
catalyst, NMO and 2,6-lutidine, olefinic bonds can be cleaved in acetone/water
to yield the corresponding carbonyl compounds.
K. C. Nicolaou, V. A. Adsool, C. R. H. Hale, Org. Lett., 2010,
12, 1552-1555.
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.
Palladium-catalyzed oxygenation of allyl arenes or alkenes produce (E)-alkenyl
aldehydes with high yields. Allylic C-H bond cleavages occur under mild
conditions during this process. Mechanistic studies show that oxygen source is
water.
H. Chen, H. Jiang, C. Cai, J. Dong, W. Fu, Org. Lett., 2011,
13, 992-994.
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.
The use of Oxone allows the conversion of various aryl-, heteroaryl-, alkenyl-,
and alkyltrifluoroborates into the corresponding oxidized products in excellent
yields. This method tolerates a broad range of functional groups, and in
secondary alkyl substrates it was demonstrated to be completely stereospecific.
G. A. Molander, L. N. Cavalcanti, J. Org. Chem., 2011,
76, 623-630.
