Single–carbon atom transfer to α,β-unsaturated amides from N-heterocyclic carbenes
- 3 February 2023
- journal article
- research article
- Published by American Association for the Advancement of Science (AAAS) in Science
- Vol. 379 (6631) , 484-488
Abstract
Single–carbon atom transfer reactions are lacking in organic synthesis, partly because of the absence of atomic carbon sources under standard solution-phase conditions. We report here that N-heterocyclic carbenes can serve as atomic carbon donors through the loss of a 1,2-diimine moiety. This strategy is applicable to single–carbon atom transfer to α,β-unsaturated amides, which can be converted into homologated γ-lactams through the formation of four single bonds to one carbon center in one operation.Keywords
This publication has 43 references indexed in Scilit:
- Ruthenium Nanoparticles Stabilized by N‐Heterocyclic Carbenes: Ligand Location and Influence on ReactivityAngewandte Chemie International Edition, 2011
- pKas of the conjugate acids of N-heterocyclic carbenes in waterChemical Communications, 2010
- Partial Deuterium Labeling of Dimethacrylate MonomersMonatshefte für Chemie - Chemical Monthly, 2006
- The Reaction of Buckminsterfullerene with Diazotetrazole. Synthesis, Isolation, and Characterization of (C60)2C2The Journal of Organic Chemistry, 1998
- Mechanism of the Reaction of Atomic Carbon with Pyrrole. Evidence for the Intermediacy of a Novel Dehydropyridinium YlideJournal of the American Chemical Society, 1994
- A novel rearrangement in the reaction of carbon atoms with furanJournal of the American Chemical Society, 1979
- Chemistry and the carbon arcAccounts of Chemical Research, 1973
- Reaction of Carbon Atoms with BenzeneJournal of the American Chemical Society, 1967
- The Photolysis of Carbon Suboxide at 3000 A in the Presence of Olefins1Journal of the American Chemical Society, 1966
- THE PHOTOLYSIS OF CARBON SUBOXIDEJournal of the American Chemical Society, 1961