Gold Nanoparticle-Catalyzed Environmentally Benign Deoxygenation of Epoxides to Alkenes

Abstract

We have developed a highly efficient and green catalytic deoxygenation of epoxides to alkenes using gold nanoparticles (NPs) supported on hydrotalcite [HT: Mg6Al2CO3(OH)16] (Au/HT) with alcohols, CO/H2O or H2 as the reducing reagent. Various epoxides were selectively converted to the corresponding alkenes. Among the novel metal NPs on HT, Au/HT was found to exhibit outstanding catalytic activity for the deoxygenation reaction. Moreover, Au/HT can be separated from the reaction mixture and reused with retention of its catalytic activity and selectivity. The high catalytic performance of Au/HT was attributed to the selective formation of Au-hydride species by the cooperative effect between Au NPs and HT.

Nanosilver as a new generation of silver catalysts in organic transformations for efficient synthesis of fine chemicals

“…Notably, under the similar reaction conditions, the gold nanoparticles supported on hydrotalcite (Au/HT) gave more higher activity in this reaction than that of Ag/HT catalyst. 37 Slightly different from the alcohol-promoted deoxygenation of epoxides, Kaneda On the basis of previous findings and the silver-cerium dioxide coreshell nanocomposite (AgNPs@CeO 2 ) catalyst for reduction of nitroaromatic compounds, 28 Kaneda and coworkers 28 found that the AgNPs@CeO 2 exhibited unique reduction ability in the deoxygenation of epoxides to the corresponding alkenes (Scheme 9). Various epoxides including aromatic, aliphatic, and alicyclic epoxides were smoothly converted into the corresponding alkenes in excellent yields (94-98%) and selectivities (>99).…”

“…Catalysis Science & Technology Minireview in this reaction than the Ag/HT catalyst. 37 Slightly different from the alcohol-promoted deoxygenation of epoxides, Kaneda et al also reported that deoxygenation of aromatic epoxides to alkenes could be efficiently catalyzed by Ag/HT using CO/H 2 O as a reductant. 38 On the basis of previous findings and the silver-cerium dioxide core-shell nanocomposite (AgNPs@CeO 2 ) catalyst for reduction of nitroaromatic compounds, 28 Kaneda and coworkers 28 found that AgNPs@CeO 2 exhibited a unique reduction ability in the deoxygenation of epoxides to the corresponding alkenes (Scheme 9).…”

Highly Selective Catalytic Reduction of Nitro- to Azoarenes under Ambient Conditions

“…A basic site of the support abstracts H ? from hydroxyl group of 2-propanol followed by b-hydride transfer to Au 0 -NP thus forming [Au-H]hydride species [26,27]. The Au-hydride and H ?…”

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

“…[140] However, the development of synthetically useful reduction protocols occurred only in the last decade with the advent of nanoparticle catalysts. Hydrotalcite-supported silver [141] and gold, [142] as well as titania-supported gold nanoparticles, [143] are efficient promoters of the reduction of a variety of epoxides (Figure 11). Thanks to these contributions, the use of WGSR conditions represents one of the mildest and most efficient catalytic methods to date for this transformation.…”