Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides
| Autor: | Adrian J. Sieradzki, Aaron M. Dumas, Liam J. Donnelly |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Acylation Transition metal Nucleophile Intramolecular force Yield (chemistry) Copper catalyzed Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 18(8) |
| ISSN: | 1523-7052 |
| Popis: | α-Aminoboronate salts are interesting examples of heteroatomic species containing adjacent nucleophilic centers. We have developed an acylation/arylation reaction using 2-bromobenzoyl chlorides as bis-electrophiles that harnesses the nucleophilicity of both positions, leading to isoindolinones. The reactions proceed under mild conditions via an intramolecular, Cu-catalyzed sp(3)-sp(2) coupling, giving products in up to 95% yield. These conditions enable arylation of α,α-disubstituted aminoboronates, which are difficult to accomplish using methods based on less abundant and more expensive transition metals. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|