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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.

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Sigma-Aldrich
N,N-dimetilacetammide, suitable for HPLC, ≥99.9%
Sigma-Aldrich
N,N-dimetilacetammide, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
N,N-dimetilacetammide, ReagentPlus®, 99%
Sigma-Aldrich
N,N-dimetilacetammide, ReagentPlus®, ≥99%
Sigma-Aldrich
N,N-dimetilacetammide, anhydrous, 99.8%
Sigma-Aldrich
N,N-dimetilacetammide, suitable for peptide synthesis, ≥99.8% (GC)
Sigma-Aldrich
2-Benzylpyridine, 98%
Sigma-Aldrich
N,N-dimetilacetammide, spectrophotometric grade, ≥99%
USP
Residual Solvent Class 2 - N,N-Dimethylacetamide, United States Pharmacopeia (USP) Reference Standard
Supelco
N,N-dimetilacetammide, analytical standard
Pheniramine impurity A, European Pharmacopoeia (EP) Reference Standard