可见光光氧化还原催化介导的醛与亚胺的还原交叉偶联反应
Reductive Cross-Coupling of Aldehydes and Imines Mediated by Visible Light Photoredox Catalysis.
作者信息
Wang Rui, Ma Mengyue, Gong Xu, Fan Xinyuan, Walsh Patrick J
机构信息
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials , Nanjing Tech University , 30 South Puzhu Road , Nanjing , 211816 , P. R. China.
Roy and Diana Vagelos Laboratories, Department of Chemistry , University of Pennsylvania , 231 South 34th Street , Philadelphia , Pennsylvania 19104-6323 , United States.
出版信息
Org Lett. 2019 Jan 4;21(1):27-31. doi: 10.1021/acs.orglett.8b03394. Epub 2018 Nov 28.
Under photoredox catalysis conditions, the conventional electrophilic reactivity of ketimines is inverted to generate nucleophilic species. As a result, chemoselective cross-electrophile couplings between aldehydes and ketimines are achieved via umpolung reactivity of ketimines to furnish amino alcohols (44 examples with good to excellent yields). To illustrate the utility of the amino alcohol products, 1,2-dihydroindol-3-one-based fluorophores are easily synthesized using the coupling products. Finally, a plausible reaction pathway is discussed.
在光氧化还原催化条件下，酮亚胺的传统亲电反应性发生反转，生成亲核物种。结果，通过酮亚胺的极性翻转反应，实现了醛与酮亚胺之间的化学选择性交叉亲电偶联，以提供氨基醇（44个实例，产率良好至优异）。为了说明氨基醇产物的实用性，使用偶联产物很容易合成基于1,2-二氢吲哚-3-酮的荧光团。最后，讨论了一个合理的反应途径。
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