Aldehydes as Alkylating Agents for Ketones. Issue 71 (19th November 2019)

• Record Type: Journal Article
• Authors: Runikhina, Sofiya A.; Afanasyev, Oleg I.; Biriukov, Klim; Perekalin, Dmitry S.; Klussmann, Martin; Chusov, Denis
• Is Part Of: Chemistry. Volume 25:Issue 71(2019)
• Page Start: 16225
• Page End: 16229
• Publication Date: 2019-11-19
• Subjects: aldehydes -- alpha-alkylation -- ketones -- reductive coupling -- ruthenium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904605
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Common and non‐toxic aldehydes are proposed as reagents for alkylation of ketones instead of carcinogenic alkyl halides. The developed reductive alkylation reaction proceeds in the presence of the commercially available ruthenium catalyst [(cymene)RuCl2 ]2 (as low as 250 ppm) and carbon monoxide as the reducing agent. The reaction works well for a broad substrate scope, including aromatic and aliphatic aldehydes and ketones. It can be carried out without a solvent and often gives nearly quantitative yields of the products. This straightforward and cost‐effective method is promising not only for laboratory application but also for industry, which produces carbon monoxide as a large‐scale waste product. Abstract : Alpha‐alkylation by aldehydes ! There are enough hydrogen atoms in the substrates for reductive alkylation of ketones by aldehydes, a ketone and even an epoxide.