Blue-light induced iron-catalyzed chemoselective α-alkylation and α-olefination of arylacetonitriles with alcohols
Blue-light induced iron-catalyzed chemoselective α-alkylation and α-olefination of arylacetonitriles with alcohols
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DOI：
10.1039/d3qo01220d
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发表时间：
2023-10-18
影响因子：
5.4
通讯作者：
Zhong，Weihui
中科院分区：
文献类型：
--
作者：
Song，Dingguo;Wang，Shiliang;Zhong，Weihui
醇和腈衍生物是一类重要的骨架化合物，在有机化学和生物有机化学中有着广泛的应用。由于它们的原子经济性和容易获得的起始原料，借用氢（BH）和取代偶联（DC）策略是获得α-烷基腈和α，β-取代丙烯腈的有力且环境友好的策略。本文报道了第一个在光辐射下合成α-烷基腈和α，β-取代丙烯腈的温和而通用的方法。该反应具有底物范围广、官能团耐受性好、反应条件简单等特点（43例，产率50-88%）。值得注意的是，该方案的温和性和实用性进一步证明了通过两个级联借用氢程序的阿尼帕米的成功合成。
Alcohols and nitrile derivatives are highly important skeletons, widely applied in both organic and bioorganic chemistry. Borrowing hydrogen (BH) and dehydrogenative coupling (DC) strategies are powerful and environmentally friendly strategies for accessing α-alkyl nitriles and α,β-substituted acrylonitriles, owing to their atom economy and readily available starting materials. Herein, we have reported the first example of a mild and general protocol for the synthesis of α-alkyl nitriles and α,β-substituted acrylonitriles under photoirradiation. The reaction featured broad substrate scope with good functional group tolerance under simple conditions (43 examples, 50–88% yields). Remarkably, the mildness and practicality of this protocol were further demonstrated by the successful synthesis of anipamil via a two-cascade borrowing hydrogen procedure.