Olefin epoxidation with bis(trimethylsilyl) peroxide catalyzed by inorganic oxorhenium derivatives. Controlled release of hydrogen peroxide.
The replacement of organometallic rhenium species (e.g., CH(3)ReO(3)) by less expensive and more readily available inorganic rhenium oxides (e.g., Re(2)O(7), ReO(3)(OH), and ReO(3)) can be accomplished using bis(trimethylsilyl) peroxide (BTSP) as oxidant in place of aqueous H(2)O(2). Using a catalytic amount of a proton source, controlled release of hydrogen peroxide helps preserve sensitive peroxorhenium species and enables catalytic turnover to take place. Systematic investigation of the oxorhenium catalyst precursors, substrate scope, and effects of various additives on olefin epoxidation with BTSP are reported in this contribution.
Yudin
A K
AK
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute,10550 N. Torrey Pines Road, La Jolla, California 92037, USA. ayudin@chem.utoronto.ca
Chiang
J P
JP
Adolfsson
H
H
Copéret
C
C
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*
D000475:Alkenes; D010545:Peroxides; D011725:Pyridines; D012821:Silanes; C431476:bis(trimethylsilyl) peroxide; C015428:perrhenate; D012211:Rhenium; D006861:Hydrogen Peroxide