Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents.
Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents.
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DOI：
10.1021/ol202597b
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发表时间：
2011-10
期刊：
影响因子：
5.2
通讯作者：
Fang Zhang;Xinfang Duan
中科院分区：
文献类型：
--
作者：
Fang Zhang;Xinfang Duan
通过格氏试剂与硝基吡啶n -氧化物的反应，研究了硝基吡啶n -氧化物的易芳基化和烷基化反应。对于相同的4-硝基吡啶n -氧化物，芳化发生在2-（或6-）位置，而烷基化发生在3-位置，以可调节的位点选择性方式。在3-硝基吡啶n -氧化物反应中发现了这两个基团的协同作用。该方法可以广泛应用于构建各种吡啶类化合物，如莫西平和绿霉素A和E的全合成。
Facile arylation and alkylation of nitropyridine N-oxides were developed through the reactions of Grignard reagents with nitropyridine N-oxides. For the same 4-nitropyridine N-oxide, arylation occurred at the 2- (or 6-) position, whereas alkylation occurred at the 3-position in an adjustably site-selective manner. The cooperative action of the two groups was discovered in the reactions of 3-nitropyridine N-oxides. This protocol can find wide applications in building various pyridine compounds as illustrated in total syntheses of Emoxipin and Caerulomycin A and E.