Synthesis of (卤)-Tetrabenazine by Visible Light Photoredox Catalysis

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• 作者：Lindsey R. Orgren ; Emily E. Maverick ; Christopher C. Marvin
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：80
• 期：24
• 页码：12635-12640
• 全文大小：425K
• ISSN：1520-6904

文摘

(卤)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis鈥揌illman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon鈥揷arbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (卤)-tetrabenazine and occurred more rapidly.