Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N
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- 作者：Derek J. Schipper ; Louis-Charles Campeau ; Keith Fagnou
- 刊名：Tetrahedron
- 出版年：2009
- 出版时间：18 April 2009
- 年：2009
- 卷：65
- 期：16
- 页码：3155-3164
- 全文大小：1321 K
文摘
Site-selective direct arylation of both sp2 and sp3 sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner. The sp3 arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and a rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions.