H2-driven deoxygenation of epoxides and diols to alkenes catalyzed by methyltrioxorhenium.
Catalytic deoxygenation of epoxides and diols is underdeveloped. This reaction is appealing in the context of making value-added organics from biomass. Methyltrioxorhenium (MTO) catalyzes the conversion of epoxides and vicinal diols to olefins with dihydrogen (H(2)) as the reductant under reasonably mild conditions (150 degrees C and 80-300 psi). The only reaction byproduct is water. The reaction is selective for cis cyclic diols, signaling a mechanism of alkene extrusion from a coordinated epoxide via a metallaoxetane intermediate.
Ziegler
Jeanette E
JE
Brown Laboratory, The Center for Catalytic Conversion of Biomass to Biofuels (C3Bio), Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA.
Zdilla
Michael J
MJ
Evans
Andrew J
AJ
Abu-Omar
Mahdi M
MM
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
D000475:Alkenes; D004852:Epoxy Compounds; D009942:Organometallic Compounds; D006859:Hydrogen; C411866:methyltrioxorhenium VII; D010100:Oxygen