Categories: C=O Bond Formation > Synthesis of aldehydes >
Synthesis of aldehydes by oxidation of alkenes
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The use of tert-butyl nitrite as a simple organic redox cocatalyst
instead of copper or silver salts enabled an aldehyde-selective aerobic
Wacker-Tsuji oxidation. Various aldehydes could beg isolated as major products
in up to 30/1 regioselectivity as well as good to high yields at room
temperature.
X.-S. Ning, M.-M. Wang, C.-Z. Yao, X.-M. Chen, Y.-B. Kang, Org. Lett.,
2016, 18, 2700-2703.
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.
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.
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.