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

Gülin Erdogan; Douglas B Grotjahn

doi:10.1021/ja903519a

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

J Am Chem Soc. 2009 Aug 5;131(30):10354-5. doi: 10.1021/ja903519a.

Authors

Gülin Erdogan¹, Douglas B Grotjahn

Affiliation

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

PMID: 19585995
DOI: 10.1021/ja903519a

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acetone / chemistry
Alkenes / chemistry*
Catalysis
Cross-Linking Reagents / chemistry*
Deuterium Exchange Measurement
Deuterium Oxide / chemistry*
Isomerism
Solvents / chemistry

Substances

Alkenes
Cross-Linking Reagents
Solvents
Acetone
Deuterium Oxide