Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

Abstract

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Aerobic Oxygenation of Alkylarenes over Ultrafine Transition‐Metal‐Containing Manganese‐Based Oxides

“…Manganese oxidesh ave attracted tremendousr esearch interest because of their potentialu se as electrode materials, adsorbents, oxidants, catalysts, and catalysts upports. [16][17][18][19][20][21][22][23][24] In particular,t heir oxidation catalysis is of great interest, and thus numerousa erobic oxidation systemst hat use catalysts based on manganese oxide have been developed. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] As fora lkylarene oxygenation, several catalysts based on manganese oxide have also been reported to be highly effective (Table S2); [40][41][42][43][44] for example, Hara and colleagues reported recently that nanosized hexagonal SrMnO 3 perovskite exhibits ah igh catalytic performance for alkylarene oxygenation under relatively mild conditions (60-120 8C, 1atm O 2 ,n oa dditives).…”

“…Manganese oxides have attracted tremendous research interest because of their potential use as electrode materials, adsorbents, oxidants, catalysts, and catalyst supports . In particular, their oxidation catalysis is of great interest, and thus numerous aerobic oxidation systems that use catalysts based on manganese oxide have been developed .…”

Preparation of Cu(II)‐Containing MOF Catalyst and Application in the α, β‐Dehydrogenation of Saturated Ketones

“…It's noted that heterogeneously catalyzed α,βdehydrogenation of ketones to the corresponding α,β-unsaturated ketones has rarely been reported so far. [16] Next, we investigated the temperature. Gratifyingly, when temperature was raised from 60°C to 80°C, the yield increased from 80 % to 87 % (entry 13), further increase in temperature, the yield reduced obviously, we considered that the primary reason was the loss of the lattice solvent molecule leading to the decompose of the [Cu(H 2 L1)(NMP)]⋅NMP⋅H 2 O (I).…”

Synthesis of (E,E)-Dienones and (E,E)-Dienals via Palladium-Catalyzed γ,δ-Dehydrogenation of Enones and Enals

“…We thought if dienones or dienals could be prepared by the aerobic γ , δ -dehydrogenation of enones or enals (Scheme 1B). This strategy has two advantages: (1) the precursors, enones or enals, can be obtained readily (some of them are commercially available and they also can be easily synthesized by aldol-like condensations, α -substitution of carbonyl compounds and subsequent elimination, oxidative α , β -dehydrogenation of saturated ketones or aldehydes, and so on) (Wade, 2005, Smith and March, 2001, Nicolaou et al., 2000, Nicolaou et al., 2002, Izawa et al., 2011, Diao and Stahl, 2011, Bigi and White, 2013, Huang and Dong, 2013, Deng et al., 2014, Huang et al., 2015, Jie et al., 2016, Yoshii et al., 2016, Chen et al., 2017) and (2) dienones and dienals bearing substituent groups in various positions could be produced directly. Despite these obvious benefits, to the best our knowledge, the efficient γ , δ -dehydrogenation of enones or enals to produce conjugated dienones or dienals has not been reported so far.…”