4.8 Article

Highly Chemoselective Metal-Free Reduction of Phosphine Oxides to Phosphines

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 44, Pages 18325-18329

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja3069165

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Funding

  1. state of Mecklenburg-Vorpommern
  2. BMBF
  3. Shanghai Institute of Organic Chemistry (SIOC)-Zhejiang Medicine joint fellowship
  4. Alexander von Humboldt Foundation

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Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Bronsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)(2)MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.

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