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  • Substitution of the nitro group with Grignard reagents: facile arylation and alkenylation of pyridine N-oxides.

Substitution of the nitro group with Grignard reagents: facile arylation and alkenylation of pyridine N-oxides.

Organic letters (2012-10-20)
Fang Zhang, Song Zhang, Xin-Fang Duan
ABSTRACT

The unprecedented substitution of a nitro group with aryl or alkenyl groups of Grignard reagents affords 2-aryl or alkenylpyridine N-oxides in modest to high yields with high chemoselectivity. This protocol allows a simple and clean synthesis of various 2-substituted pyridine N-oxides and the corresponding pyridine derivatives. Furthermore, straightforward one-pot iterative functionality of pyridine N-oxides could also be achieved simply by successive applications of two Grignard reagents.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyridine N-oxide, 95%