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Synthesis of aldehydes by benzylic oxidation


Recent Literature

Cost-effective and widely applicable protocols for controlled and predictably selective oxidation of methyl-/alkylarenes to corresponding value-added carbonyls have been developed, using a surfactant-based oxodiperoxo molybdenum catalyst in water and hydrogen peroxide (H2O2) as an environmentally benign green oxidant without any external base, additive, or cocatalyst.
P. Thiruvengetam, D. K. Chand, J. Org. Chem., 2022, 87, 4061-4077.

The use of NaClO/TEMPO/Co(OAc)2 enabled a benzylic oxidation of alkyl arenes to yield various aromatic aldehydes and ketones in very good yields. The reaction reactivity, selectivity, and scope of the reaction were investigated.
C. Jin, L. Zhang, W. Su, Synlett, 2011, 1435-1438.

o-Iodoxybenzoic acid (IBX) was found to be highly effective in oxidations adjacent to carbonyl and benzylic functionalities to form either α,β-unsaturated carbonyl compounds or conjugated aromatic carbonyl systems. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates.
K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc., 2002, 124, 2245-2258.

Permanganate supported on active manganese dioxide can be used effectively for the oxidation of arenes, alcohols and sulfides under heterogeneous or solvent-free conditions.
A. Shaabania, P. Mirzaeia, S. Naderia, D. G. Leeb, Tetrahedron, 2004, 60, 11415-11420.

A copper-catalyzed aerobic oxidative decarboxylation of phenylacetic acids and α-hydroxyphenylacetic acids enables the synthesis of aromatic carbonyl compounds via decarboxylation, dioxygen activation, and C-H bond oxidation steps in a one-pot protocol with molecular oxygen as the sole terminal oxidant.
Q. Feng, Q. Song, J. Org. Chem., 2014, 79, 1867-1871.