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Transition‐Metal‐Free Regioselective Alkylation of Quinoline N‐Oxides via Oxidative Alkyl Migration and C−C Bond Cleavage of tert‐/sec‐Alcohols
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-01-05 , DOI: 10.1002/adsc.201701330
Chiranjit Sen 1 , Subhash C. Ghosh 1
Affiliation  

An unprecedented C2‐alkylation of quinoline N‐oxide derivatives via C−C bond activation of tert‐ and sec‐alkyl alcohol is described using hypervalent iodine (III) reagent PhI(OAc)2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents is more practical, operationally simple and transition metal free. The reaction proceeds efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N‐oxides using a variety of tert‐/sec‐ alcohols. From experimental outcome, we also propose a rationalized mechanism, mediated by PIDA.

中文翻译:

通过叔烷基/仲醇的氧化烷基转移和C-C键裂解实现喹啉N-氧化物的无过渡金属区域选择性烷基化

喹啉N-氧化物衍生物的前所未有的C2烷基化通过C-C键活化的烷基醇是使用高价碘(III)试剂岛(OAC)描述2(PIDA)。使用温和的高价碘试剂进行的区域选择性烷基化反应更加实用,操作简单且不含过渡金属。使用多种/醇,反应可在多种底物(包括喹啉,异喹啉和吡啶N-氧化物)上有效地进行。从实验结果来看,我们还提出了一种由PIDA调解的合理化机制。
更新日期:2018-01-05
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