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6.1.38.14.4 Variation 4: Oxidation to Acids

DOI: 10.1055/sos-SD-006-00903

Zaidlewicz, M.; Krzeminski, M.Science of Synthesis, (200561145.

Trialkylboranes containing primary alkyl groups can be transformed into carboxylic acids in excellent yields by oxidation with pyridinium dichromate in dimethylformamide, sodium dichromate in aqueous sulfuric acid, or chromium trioxide in 90% aqueous acetic acid.[‌328‌] Oxidations with the first two reagents afford 7080% yields of carboxylic acids, whereas chromium trioxide achieves similar oxidations very cleanly affording carboxylic acids 57 in 8092% yields (Scheme 95).[‌328‌,‌329‌]

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References