Organic Letters 2011-11-18

Facile one-pot direct arylation and alkylation of nitropyridine N-oxides with Grignard reagents.

Fang Zhang, Xin-Fang Duan

Index: Org. Lett. 13(22) , 6102-5, (2011)

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Abstract

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.