A new mild oxidation of amines to aldehydes and ketones. Part II

✍ Scribed by Huai Gu Chen; Paul Knochel

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 123 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82432-6

✦ Synopsis

Summm:

The silylamines 1, after conversion into their lithium or zinc salts, were readily oxidized by dry air under very mild conditions (-60' C to -20' C, 5-45 min.) into the corresponding aldehydes or ketones 2 in good yields. Our reaction conditions tolerate the presence of other oxidation sensitive functional groups like a phosphine, a thioether or a tertiary amine.

Recently we reported that l,l-diorganometalhcs of tin, silicon and zinc are readily oxidized by dry air into aldehydes and ketones in good yieldsl. We found that this reaction could be extended to metallated silylamines (see Scheme 1).

Method B:

A solution of ZnBr2 (1.35 g; 6.0 mmol) in 5 ml of THF was added to the lithiated silylamine prior to the oxidation which was performed at -20' C for 35 min. and afforded 0.48 g (81%) of pure norbomanone.