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- Title
Efficient Base‐Catalyzed Hydrosilylation of Tertiary Amides to Aldehydes.
- Authors
Clarke, Joshua A.; Nikonov, Georgii I.
- Abstract
A chemoselective catalytic reduction of tertiary amides to aldehydes is reported. The catalytic system KOtBu/(EtO)2MeSiH has been found to be highly active in the conversion of tertiary amides to silylated hemiaminals, which after acidic work‐up yields the respective aldehydes under mild conditions. The use of amides containing α‐protons in this catalytic reaction resulted in elimination to furnish enamines characterized by 1H‐NMR. This mild and selective process is compatible with nitriles, ethers, amines, and heterocyclic functionalities. However, competition experiments revealed poor tolerance for easily reducible functional groups, such as esters, ketones, and aldehydes. This transition metal‐free strategy presents a cheap and readily available process for the efficient reduction of tertiary amides to the corresponding aldehydes.
- Subjects
ALDEHYDES; HYDROSILYLATION; ENAMINES; AMIDES; ELIMINATION reactions; HEMIAMINALS; CATALYTIC reduction
- Publication
ChemCatChem, 2022, Vol 14, Issue 24, p1
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.202201231