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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.

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

Abstract

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.

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