Progress in the Study of Dehydroxymethylation of Primary Alcohol

doi:10.6023/cjoc202303009

Abstract

Primary alcohols are abundant and readily available, which have been widely used as feedstock chemicals for the synthesis of agrochemicals, food additives, fragrances, pharmaceuticals and so on. The dehydroxymethylation reaction is an effective strategy to prepare hydrocarbons with one less carbon atom from primary alcohols, which has attracted tremendous attentions of many organic chemists and applied in biomass degradation and drug synthesis. The development of dehydroxy- methylation of primary alcohol on the base of the reaction characters is reviewed, including transition-metal catalyzed dehydroxymethylation to access methane and water, transition-metal catalyzed dehydroxymethylation to produce carbon monoxide and hydrogen, transition-metal catalyzed dehydroxymethylation to generate formaldehyde, as well as transition-metal free dehydroxymethylation to furnish formic acid and water. Each type of reaction is systematically summarized according to the catalytic system, the substrates scope and reaction mechanism.

Key words: primary alcohol, dehydroxymethylation, transition-metal catalyzed, hydrocarbon

Cite this article

Xinqiang Chen, Jing Zhang. Progress in the Study of Dehydroxymethylation of Primary Alcohol[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2711-2719.

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Fig. & Tab. 13

Scheme 1. Methods for dehydroxymethylation of primary alcohol

Scheme 2. Nickel catalyzed dehydroxymethylation of primary alcohol

Scheme 3. Ru/TiO2 catalyzed dehydroxymethylation of primary alcohol

Scheme 4. Ru/CeO2 catalyzed dehydroxymethylation of primary alcohol

Scheme 5. Bimetallic catalyzed dehydroxymethylation of primary alcohol

Scheme 6. Mechanism of iridium catalyzed dehydroxymethylation of primary alcohol

Scheme 7. Mechanism of rhodium catalyzed dehydroxymethylation of primary alcohol

Scheme 8. Palladium catalyzed dehydroxymethylation of primary alcohol

Scheme 9. Mechanism of palladium catalyzed dehydroxymethylation of primary alcohol

Scheme 10. Mechanism of palladium catalyzed dehydroxy- methylation of primary alcohol

Scheme 11. Dehydroxymethylation of primary alcohol

Scheme 12. Mechanism of CeCl3 catalyzed dehydroxymethylation of primary alcohol

Scheme 13. Mechanism of metal-free catalyzed dehydroxy- methylation of heteroaryl primary alcohol

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