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Visible-Light-Mediated Three-Component Decarboxylative Coupling Reactions for the Synthesis of 4-Alkylpyridines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-14 , DOI: 10.1021/acs.joc.4c02037 Ai Wang, Yijian Ma, Jia-Hui Jin, Le-Quan Wang, Dan-Dan Li, Zi-Wei Xi, Chengshuo Shen, Yong-Miao Shen
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-11-14 , DOI: 10.1021/acs.joc.4c02037 Ai Wang, Yijian Ma, Jia-Hui Jin, Le-Quan Wang, Dan-Dan Li, Zi-Wei Xi, Chengshuo Shen, Yong-Miao Shen
4-Alkylation of pyridines has been achieved by a photocatalyzed three-component reaction of an olefin, an aryloxyacetic acid, and cyanopyridine using Ir[dF(CF3)ppy]2(dtbbpy)PF6 as a photocatalyst. In this way, a new type of 4-alkylpyridines bearing aryl and aryloxy substituents on the phenyl was accessed with potential pharmaceutical value. In addition to mild reaction conditions, the method has several other advantages, including a multicomponent one-pot protocol, good functional group tolerance, and easy amplification of the reaction scale. The reaction mechanism has been clarified by control experiments and computation of the reaction energy profile.
中文翻译:
可见光介导的三组分脱羧偶联反应合成 4-烷基吡啶
吡啶的 4-烷基化是通过烯烃、芳氧基乙酸和氰基吡啶的光催化三组分反应实现的,使用 Ir[dF(CF3)ppy]2(dtbbpy)PF6 作为光催化剂。通过这种方式,一种在苯基上带有芳基和芳氧基取代基的新型 4-烷基吡啶被获得,具有潜在的药学价值。除了温和的反应条件外,该方法还具有其他几个优点,包括多组分一锅方案、良好的官能团耐受性以及易于扩增反应规模。通过对照实验和反应能量曲线的计算阐明了反应机理。
更新日期:2024-11-14
中文翻译:
可见光介导的三组分脱羧偶联反应合成 4-烷基吡啶
吡啶的 4-烷基化是通过烯烃、芳氧基乙酸和氰基吡啶的光催化三组分反应实现的,使用 Ir[dF(CF3)ppy]2(dtbbpy)PF6 作为光催化剂。通过这种方式,一种在苯基上带有芳基和芳氧基取代基的新型 4-烷基吡啶被获得,具有潜在的药学价值。除了温和的反应条件外,该方法还具有其他几个优点,包括多组分一锅方案、良好的官能团耐受性以及易于扩增反应规模。通过对照实验和反应能量曲线的计算阐明了反应机理。