4.8 Article

General and Selective Copper-Catalyzed Reduction of Tertiary and Secondary Phosphine Oxides: Convenient Synthesis of Phosphines

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 23, Pages 9727-9732

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja301764m

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Funding

  1. state of Mecklenburg-Vorpommern
  2. BMBF
  3. Shanghai Institute of Organic Chemistry (SIOC)-Zhejiang Medicine

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Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination domino sequence allows for the synthesis of a variety of functionalized aromatic and aliphatic phosphines in good yields.

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