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

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

Organic letters (2014-03-22)

Masaki Itoh, Koji Hirano, Tetsuya Satoh, Masahiro Miura

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.

MATERIALS

Product Number

Brand

Product Description

B30200

Sigma-Aldrich

2-Benzylpyridine, 98%

Y0001428

Pheniramine impurity A, European Pharmacopoeia (EP) Reference Standard

17308

Sigma-Aldrich

N,N-Dimethylacetamide, suitable for peptide synthesis, ≥99.8% (GC)