Cobalt-Catalyzed Cross-Coupling of Grignards with Allylic and Vinylic Bromides: Use of Sarcosine as a Natural Ligand

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• 作者：Rok Frlan ; Matej Sova ; Stanislav Gobec ; Gaj Stavber ; Zdenko 膶asar
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：80
• 期：15
• 页码：7803-7809
• 全文大小：489K
• ISSN：1520-6904

文摘

Sarcosine was discovered to be an excellent ligand for cobalt-catalyzed carbon鈥揷arbon cross-coupling of Grignard reagents with allylic and vinylic bromides. The Co(II)/sarcosine catalytic system is shown to perform efficiently when phenyl and benzyl Grignards are coupled with alkenyl bromides. Notably, previously unachievable Co-catalyzed coupling of allylic bromides with Grignards to linearly coupled 伪-products was also realized with Co(II)/sarcosine catalyst. This method was used for efficient preparation of the key intermediate in an alternative synthesis of the antihyperglycemic drug sitagliptin.