Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
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DOI：
10.1021/acs.orglett.7b02395
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发表时间：
2017-09-01
期刊：
影响因子：
5.2
通讯作者：
Bode, Jeffrey W.
中科院分区：
文献类型：
--
作者：
Jackl, Moritz K.;Legnani, Luca;Bode, Jeffrey W.
醛和硅胺方案（SIBR）试剂的光催化偶联使得能够在连续流动条件下简单、可规模化地合成取代的吗啉、氧氮杂环庚烷、硫代吗啉和硫氮杂环庚烷。该方法成功的关键是廉价的有机光催化剂（TPP）和刘易斯酸添加剂的组合，其形成易于还原以完成催化循环的胺自由基阳离子。二-和三取代的SISTORIC试剂通过烯烃的铁催化的氨基醚化在一个步骤中形成。
Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.