4.6 Article

Copper-catalyzed C-alkylation of secondary alcohols and methyl ketones with alcohols employing the aerobic relay race methodology

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 15, Pages 2973-2978

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ob06739g

Keywords

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Funding

  1. NNSFC [20902070]
  2. SRF for ROCS of SEM, NSF [Y4100579]
  3. QJTP of Zhejiang Province [QJD0902004]

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By employing aerobic oxidation to aldehydes as a more effective alcohol activation strategy, ligand-free copper catalysts were found to be superior catalysts than other metals in aerobic dehydrative beta-alkylation of secondary alcohols and alpha-alkylation of methyl ketones using alcohols as the green alkylating reagents. Based on our mechanistic studies and also supported by the literature, we deduce that the newly-proposed relay race process rather than the conventional borrowing hydrogen-type mechanisms should be the most possible and a more rational mechanism for the aerobic C-alkylation reactions.

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