Copper-catalyzed α-methylenation of benzylpyridines using dimethylacetamide as one-carbon source

Masaki Itoh; Koji Hirano; Tetsuya Satoh; Masahiro Miura

doi:10.1021/ol500655k

Copper-catalyzed α-methylenation of benzylpyridines using dimethylacetamide as one-carbon source

Org Lett. 2014 Apr 4;16(7):2050-3. doi: 10.1021/ol500655k. Epub 2014 Mar 19.

Authors

Masaki Itoh¹, Koji Hirano, Tetsuya Satoh, Masahiro Miura

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

PMID: 24646166
DOI: 10.1021/ol500655k

Abstract

The direct α-methylenation of benzylpyridines was achieved using N,N-dimethylacetamide (DMA) as a one-carbon source under copper catalysis. An intermediary species was detected at an early stage, and a possible mechanism was proposed. Additionally, α-oxygenation and dimerization of benzylpyridines could also be performed efficiently.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetamides / chemistry*
Benzyl Compounds / chemistry*
Carbon / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Copper / chemistry*
Molecular Structure
Pyridines / chemistry*
Stereoisomerism

Substances

Acetamides
Benzyl Compounds
Pyridines
Carbon
Copper
2-benzylpyridine
dimethylacetamide