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  • 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
PMID24646166
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
1601485
USP
Residual Solvent Class 2 - N,N-Dimethylacetamide, United States Pharmacopeia (USP) Reference Standard
Y0001428
Pheniramine impurity A, European Pharmacopoeia (EP) Reference Standard
B30200
Sigma-Aldrich
2-Benzylpyridine, 98%
07-4072
Sigma-Aldrich
N,N-Dimethylacetamide, SAJ first grade, ≥99.0%
07-4071
Sigma-Aldrich
N,N-Dimethylacetamide, SAJ special grade
72336
Supelco
N,N-Dimethylacetamide, analytical standard
185884
Sigma-Aldrich
N,N-Dimethylacetamide, ReagentPlus®, ≥99%
17308
Sigma-Aldrich
N,N-Dimethylacetamide, suitable for peptide synthesis, ≥99.8% (GC)
271012
Sigma-Aldrich
N,N-Dimethylacetamide, anhydrous, 99.8%
154806
Sigma-Aldrich
N,N-Dimethylacetamide, spectrophotometric grade, ≥99%
D137510
Sigma-Aldrich
N,N-Dimethylacetamide, ReagentPlus®, 99%
38840
Sigma-Aldrich
N,N-Dimethylacetamide, puriss. p.a., ≥99.5% (GC)
270555
Sigma-Aldrich
N,N-Dimethylacetamide, suitable for HPLC, ≥99.9%