化学
芳构化
烷基
氧化还原
部分
催化作用
氘
功能群
劈理(地质)
组合化学
立体化学
药物化学
有机化学
物理
聚合物
岩土工程
量子力学
断裂(地质)
工程类
作者
Xukai Zhou,Tao Yu,Guangbin Dong
摘要
Deuterated organic compounds have become increasingly important in many areas; however, it remains challenging to install deuterium site-selectively to unactivated aliphatic positions with control of the degree of deuteration. Here, we report a Cu-catalyzed degree-controlled deacylative deuteration of diverse alkyl groups with the methylketone (acetyl) moiety as a traceless activating group. The use of N-methylpicolino-hydrazonamide (MPHA) promotes efficient aromatization-driven C-C cleavage. Mono-, di-, and trideuteration at specific sites can be selectively achieved. The reaction is redox-neutral with broad functional group tolerance. The utility of this method has been demonstrated in forming a complete set of deuterated ethyl groups, merging with the Diels-Alder reaction, a net devinylative deuteration, and the synthesis of the d2-analogue of Austedo.
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