Fe(NO3)3/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): An efficient catalyst system for selective oxidation of alcohols under aerobic conditions

Hu, Yongke; Chen, Lei; Li, Bindong

doi:10.1016/j.catcom.2017.09.019

Cited by 38 publications

(18 citation statements)

References 33 publications

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“…According to the reported results, the valence transformation of metal iron such as Mn III /Mn II (Yang et al, 2014;Fei et al, 2017;Gurrala et al, 2018), Co III /Co II (Zhou et al, 2015;Cordoba et al, 2017;Li et al, 2017), Cr III / Cr II (Thao et al, 2018) could catalyze the oxidation of alcohols. Especially, the transformation of Fe 3+ /Fe 2+ possessed high catalytic activity by initiating a series of electron transfer (Hu et al, 2016(Hu et al, , 2018Miao et al, 2016). Combined with above results, Fe 3+ could be regard as a catalyst and the electron transfer between of Fe 3+ and Fe 2+ would catalyze the oxidation process.…”

Section: No −mentioning

confidence: 62%

“…On the one hand, NO − 3 could produce NO 2 , and then NO 2 with H 2 O was converted to HNO 2 , which had been proved as a pivotal role in benzyl alcohol oxidation (Aellig et al, 2012;Luo et al, 2012). On the other hand, the valence change of Fe could catalyze benzyl alcohol oxidation according to the literatures (Miao et al, 2016;Hu et al, 2018). Coincidentally, the transformation between Fe 3+ and Fe 2+ was demonstrated by the K 3 [Fe(CN) 6 ] solution.…”

Section: The Product Analysismentioning

confidence: 97%

“…Finally, the function of NO x was investigated by a series of auxiliary experiments. As we know, nitric oxide (NO) would be immediately oxidized to nitrogen dioxide (NO 2 ) by O 2 (Wang et al, 2005;Shen et al, 2015Shen et al, , 2019Miao et al, 2016;Hu et al, 2018;Dong et al, 2019;Zhao et al, 2019). O 2 was flowed into the reaction system in the experimental process to detect the NO.…”

Section: No −mentioning

confidence: 99%

“…Moreover, the catalytic activity of heterogeneous catalysts would be lower than their homogeneous counterparts after several recycles (Parmeggiani and Camilla, 2012). Hence, the metal-based homogeneous catalysts, including Ru (Shimizu et al, 2005), V (Hanson et al, 2008), Cu (Hansen et al, 2013;Jia et al, 2014), and Fe (Jiang et al, 2016;Li et al, 2016;Miao et al, 2016;Hu et al, 2018), continued to gain great interests.…”

Section: Introductionmentioning

confidence: 99%

“…Among those homogenous catalysts, non-toxic, abundant, and bio-friendly, iron-based metals have widely aroused attentions (Martin and Suárez, 2002;Wang et al, 2005;Zhang et al, 2013;Hu et al, 2016Hu et al, , 2018. Zhang and co-workers reported a series of Fe catalysts, such as FeBr 3 , Fe 2 O 3 , and Fe 2 (SO 4 ) 3 , with performance catalyzing benzylamine to imine in air atmosphere (Zhang et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

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Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde by Nitrates

Huang

et al. 2020

Front. Chem.

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In this paper, ferric nitrate was used to oxidize benzyl alcohol in a mild condition and demonstrated its better performance compared to HNO 3. In the reaction, the conversion rate and product selectivity could be both as high as 95% in N 2 atmosphere, while the benzaldehyde yield also reached 85% in air. Similar to Fe(NO 3) 3 •9H 2 O, the other metallic nitrates such as Al(NO 3) 3 •9H 2 O and Cu(NO 3) 2 •3H 2 O could also oxidize the benzyl alcohol with high activity. The applicability of Fe(NO 3) 3 •9H 2 O for other benzylic alcohol was also investigated, and the reaction condition was optimized at the same time. The results showed the Fe(NO 3) 3 •9H 2 O would be more conducive in oxidizing benzyl alcohol under the anaerobic condition. The experiments in N 2 or O 2 atmospheres were conducted separately to study the catalytic mechanism of Fe(NO 3) 3. The results showed the coexistence of Fe 3+ and NO − 3 will generate high activity, while either was with negligible oxidation property. The cyclic transformation of Fe 3+ and Fe 2+ provided the catalytic action to the benzyl alcohol oxidation. The role of NO − 3 was also an oxidant, by providing HNO 2 in anaerobic condition, while NO − 3 would be regenerated from NO in aerobic condition. O 2 did not oxidize the benzyl alcohol conversion directly, while it could still be beneficial to the procedure by eliminating the unwelcome NO and simultaneously reinforcing the circulation of Fe 2+ and Fe 3+ , which therefore forms a green cyclic oxidation. Hence, the benzyl alcohol oxidation was suggested in an air atmosphere for efficiency and the need of green synthesis.

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Section: No −mentioning

confidence: 62%

Section: The Product Analysismentioning

confidence: 97%

Section: No −mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde by Nitrates

Huang

et al. 2020

Front. Chem.

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Chemoselective and ligand‐free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina‐supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst

Das

Nandy

Bhar

2021

Applied Organom Chemis

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An economically efficient and operationally simple ligand‐free protocol for the chemoselective oxidation of benzylic alcohols to carbonyl compounds has been developed using alumina‐supported nickel nanoparticles as a stable recyclable heterogeneous catalyst along with potassium tert‐butoxide in the presence of aerial oxygen as an eco‐friendly oxidant. The aliphatic alcohols remained unaffected under the present condition. Excellent chemoselectivity has also been demonstrated through intermolecular and intramolecular competition experiments. This protocol accommodates a diverse range of substituents with the tolerance of various sensitive moieties during the reaction. The catalyst could be recovered by filtration and reused consecutively without any significant loss in the catalytic activity. Moreover, the heterogeneity of the catalyst has also been established by the “hot filtration method (Sheldon's test)”.

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Iron‐Based Multi‐Catalysis: Eco‐Compatible Alternative for Complex Molecules Synthesis

Quintard

2020

Chemistry A European J

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Fe(NO3)3/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): An efficient catalyst system for selective oxidation of alcohols under aerobic conditions

Cited by 38 publications

References 33 publications

Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde by Nitrates

Selective Catalytic Oxidation of Benzyl Alcohol to Benzaldehyde by Nitrates

Chemoselective and ligand‐free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina‐supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst

Iron‐Based Multi‐Catalysis: Eco‐Compatible Alternative for Complex Molecules Synthesis

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