Mild and selective deuteration and isomerization of alkenes by a bifunctional catalyst and deuterium oxide.
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.
Erdogan
Gülin
G
Department of Chemistry and Biochemistry, 5500 Campanile Drive, San Diego State University, San Diego California 92182-1030, USA.
Grotjahn
Douglas B
DB
D000096:Acetone / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D041961:Deuterium Exchange Measurement; D017666:Deuterium Oxide / Q000737:chemistry*; D007536:Isomerism; D012997:Solvents / Q000737:chemistry
D000475:Alkenes; D003432:Cross-Linking Reagents; D012997:Solvents; D000096:Acetone; D017666:Deuterium Oxide