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Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins

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Title: Discovery and optimization of rapid manganese catalysts for the epoxidation of terminal olefins
Authors: Murphy, Andrew1, Stack, T. Daniel P. stack@stanford.edu
Source: Journal of Molecular Catalysis A: Chemistry. May2006, Vol. 251 Issue 1/2, p78-88. 11p.
Subjects: Manganese catalysts, Alkenes, Epoxy compounds, Peracetic acid
Abstract: Abstract: Twenty-two MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid as the oxidant. A limited number of these complexes are efficient catalysts using peracetic acid solutions generated with H2SO4 (PAAC), but most complexes are effective at 1mol% catalyst loading using peracetic acid generated with strongly acidic resins (PAAR). Under the less acidic conditions of PAAR, [MnII(phen)2(CF3SO3)2] has the highest activity of the catalysts screened, and epoxides terminal olefins using as little as 0.02mol% catalyst within 5min. The dimeric species [MnIII,IV 2(phen)4(O)2](ClO4)3 is also a viable epoxidation catalyst with PAAR, but the dimeric species is reduced by the residual H2O2 to monomeric MnII species under the reaction conditions. By comparison, a similar dimeric complex [MnIII,IV 2(R,R-mcp)2(O)2](ClO4)3, is not reduced by H2O2 under the reaction conditions and is not catalytically active, supportive of the notion that the catalytically relevant species is monomeric. [Copyright &y& Elsevier]
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Abstract:Abstract: Twenty-two MnII complexes were screened for the catalytic epoxidation of terminal olefins using peracetic acid as the oxidant. A limited number of these complexes are efficient catalysts using peracetic acid solutions generated with H2SO4 (PAAC), but most complexes are effective at 1mol% catalyst loading using peracetic acid generated with strongly acidic resins (PAAR). Under the less acidic conditions of PAAR, [MnII(phen)2(CF3SO3)2] has the highest activity of the catalysts screened, and epoxides terminal olefins using as little as 0.02mol% catalyst within 5min. The dimeric species [MnIII,IV 2(phen)4(O)2](ClO4)3 is also a viable epoxidation catalyst with PAAR, but the dimeric species is reduced by the residual H2O2 to monomeric MnII species under the reaction conditions. By comparison, a similar dimeric complex [MnIII,IV 2(R,R-mcp)2(O)2](ClO4)3, is not reduced by H2O2 under the reaction conditions and is not catalytically active, supportive of the notion that the catalytically relevant species is monomeric. [Copyright &y& Elsevier]
ISSN:13811169
DOI:10.1016/j.molcata.2006.01.042