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Literature DB >> 16366550

A solution to the 2-pyridyl organometallic cross-coupling problem: regioselective catalytic direct arylation of pyridine N-oxides.

Louis-Charles Campeau¹, Sophie Rousseaux, Keith Fagnou.

Abstract

Direct arylation reactions of pyridine N-oxides occur in excellent yield with complete selectivity for the 2-position with a wide range of aryl bromides. This reactivity permits the use of inexpensive, commercially available, and bench-stable pyridine N-oxides as replacements for problematic 2-metallapyridines in palladium-catalyzed cross-coupling reactions.

Entities: Chemical

Year: 2005 PMID： 16366550 DOI： 10.1021/ja056800x

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

42 in total

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors: Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal: J Am Chem Soc Date: 2011-09-22 Impact factor: 15.419

2. Rh(I)-catalyzed direct arylation of azines.

Authors: Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal: J Org Chem Date: 2010-10-29 Impact factor: 4.354

3. Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers.

Authors: Yichen Tan; Fabiola Barrios-Landeros; John F Hartwig
Journal: J Am Chem Soc Date: 2012-02-17 Impact factor: 15.419

A solution to the 2-pyridyl organometallic cross-coupling problem: regioselective catalytic direct arylation of pyridine N-oxides.

1. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

2. Rh(I)-catalyzed direct arylation of azines.

3. Mechanistic studies on direct arylation of pyridine N-oxide: evidence for cooperative catalysis between two distinct palladium centers.

Review 4. Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

5. Direct palladium-catalyzed alkynylation of N-fused heterocycles.

6. Copper-catalyzed arylation of heterocycle C-H bonds.

7. Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate.

8. Pd0/PR3-catalyzed arylation of nicotinic and isonicotinic acid derivatives.

9. Rh(I)-catalyzed direct arylation of pyridines and quinolines.

10. Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.