Counterintuitive chemoselectivity in the reduction of carbonyl compounds.

Autor: Iwasaki T; Department of Chemistry and Biotechnology, The University of Tokyo, Tokyo, Japan. iwasaki@chembio.t.u-tokyo.ac.jp., Nozaki K; Department of Chemistry and Biotechnology, The University of Tokyo, Tokyo, Japan.
Jazyk: angličtina
Zdroj: Nature reviews. Chemistry [Nat Rev Chem] 2024 Jul; Vol. 8 (7), pp. 518-534. Date of Electronic Publication: 2024 Jun 03.
DOI: 10.1038/s41570-024-00608-z
Abstrakt: The reactivity of carbonyl functional groups largely depends on the substituents on the carbon atom. Reversal of the commonly accepted order of reactivity of different carbonyl compounds requires novel synthetic approaches. Achieving selective reduction will enable the transformation of carbon resources such as plastic waste, carbon dioxide and biomass into valuable chemicals. In this Review, we explore the reduction of less reactive carbonyl groups in the presence of those typically considered more reactive. We discuss reductions, including the controlled reduction of ureas, amides and esters to aldehydes, as well as chemoselective reductions of carbonyl groups, including the reduction of ureas over carbamates, amides and esters; the reduction of amides over esters, ketones and aldehydes; and the reduction of ketones over aldehydes.
(© 2024. Springer Nature Limited.)
Databáze: MEDLINE
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