𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Direct formation of functionalized ketones via the coupling of functionalized organocopper reagents with acid chlorides

✍ Scribed by Richard M. Wehmeyer; Reuben D. Rieke

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
303 KB
Volume
29
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Highly reactive copper solutions have been prepared by the lithium naphthalide reduction of a copper(I) iodide/triphenyl-phosphine complex. These copper solutions react rapidly with functionalized alkyl halides to give organocopper reagents which have been effectively trapped with acid chlorides giving functionalized ketones in good yields. Ester, nitrile, chloride, remote epoxide, and, to some degree, ketone groups can be tolerated by this approach.

πŸ“œ SIMILAR VOLUMES

A novel synthesis of functionalized keto
A novel synthesis of functionalized ketones via a nickel-catalyzed coupling reaction of zinc reagents with thiolesters
✍ Toshiaki Shimizu; Masahiko Seki πŸ“‚ Article πŸ“… 2002 πŸ› Elsevier Science 🌐 French βš– 62 KB

N Ph(CH 2 ) 3 COS DMF Ph(CH 2 ) 3 O n-Bu n-BuI + NiCl 2 , Zn 50 o C, 5 h 2 46% 1 DMF (CH 2 ) 2 COSEt MeO MeO O (CH 2 ) 4 -CO 2 Et (CH 2 ) 2 + I-(CH 2 ) 4 -CO 2 Et 3a 6 5a NiCl 2 , Zn 50 o C, 5 h TETRAHEDRON LETTERS