Send to

Choose Destination
See comment in PubMed Commons below
J Am Chem Soc. 2009 Aug 5;131(30):10354-5. doi: 10.1021/ja903519a.

Mild and selective deuteration and isomerization of alkenes by a bifunctional catalyst and deuterium oxide.

Author information

  • 1Department of Chemistry and Biochemistry, 5500 Campanile Drive, San Diego State University, San Diego California 92182-1030, USA.


H/D exchange is achieved at allylic positions of alkenes using D(2)O in acetone and alkene isomerization catalyst 1, which features a bifunctional imidazolylphosphine. The basic nitrogen of the latter is thought to deprotonate an alkene substrate coordinated to the CpRu center; at this stage the protonated nitrogen could undergo H/D exchange with deuterium oxide. An exceptional degree of deuteration is achieved at positions accessible to isomerization, with a high degree of control. Using biphasic settings one can literally wash out reactive protons on the substrate without using organic solvents.

[PubMed - indexed for MEDLINE]
PubMed Commons home

PubMed Commons

How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Write to the Help Desk