Mixed copper, zinc 2-amino benzylic organometallics as efficient reagents for the synthesis of heterocycles

✍ Scribed by Huai Gu Chen; Craig Hoechstetter; Paul Knochel

• Book ID: 104232953
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 278 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80510-4

✦ Synopsis

The mixed copper, zinc benzylic organometallics la-k react efficiently with various electrophiles. By the reaction with acyl chlorides, highly functionalized 2-substituted indoles are produced. The treatment of la with allylic bromides, 3-iodo-cyclohexenone and ethyl propiolate furnishes polyfunctionalized anilines. Several of them could be converted into five-or seven-membered heterocycles.

The low reactivity of the carbon-zinc bond allows the preparation of highly functionalized zinc organometallics having a broad synthetic potentiallT2. We recendy reported a general preparation of benzylic zinc halides3 and showed that after