Decarboxylative N-Alkylation of Azoles through Visible-Light-Mediated Organophotoredox Catalysis
Decarboxylative N-Alkylation of Azoles through Visible-Light-Mediated Organophotoredox Catalysis
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DOI：
10.1021/acs.orglett.1c01745
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发表时间：
2021-06-17
期刊：
影响因子：
5.2
通讯作者：
Ohmiya, Hirohisa
中科院分区：
文献类型：
--
作者：
Kobayashi, Rino;Shibutani, Shotaro;Ohmiya, Hirohisa
一个有机光氧化还原催化脱羧亲核试剂和脂肪族羧酸衍生的氧化还原活性酯之间的交叉偶联被证明。该方案在温和和无过渡金属的条件下有效地将各种叔或仲烷基片段安装到唑类亲核试剂的氮原子上。吡啶鎓添加剂成功地抑制了碳阳离子中间体的消除副产物的形成。该反应适用于含唑类和沙利度胺的蛋白质降解剂样分子的合成。
An organophotoredox-catalyzed decarboxylative cross-coupling between azole nucleophiles and aliphatic carboxylic acid-derived redox-active esters is demonstrated. This protocol efficiently installs various tertiary or secondary alkyl fragments onto the nitrogen atom of azole nucleophiles under mild and transition-metal-free conditions. The pyridinium additive successfully inhibits the formation of elimination byproducts from the carbocation intermediate. This reaction is applicable to the synthesis of a protein-degrader-like molecule containing an azole and a thalidomide.