Photochemical oxidation of alcohols to ketones or aldehydes using DMSO as an oxidant without activated agent

被引：12

作者：

Zhao, Jinwu ^{[1
]}

Luo, Zhigao ^{[1
]}

Liu, Yipeng ^{[1
]}

Xu, Jingxiu ^{[1
]}

Huang, Zunnan ^{[2
]}

Xiong, Wenfang ^{[1
]}

机构：

[1] Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China

[2] Guangdong Med Univ, Lab Res & Dev Nat Drugs Guangdong Prov, Dongguan 523808, Peoples R China

来源：

TETRAHEDRON | 2023年 / 131卷

基金：

中国国家自然科学基金;

关键词：

Oxidation; Alcohol; DMSO; Visible light; Metal; -free; SELECTIVE OXIDATION; AEROBIC OXIDATION; DEHYDROGENATION; CATALYST; FRAMEWORKS; AIR;

D O I：

10.1016/j.tet.2022.133208

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report visible light mediated oxidation of alcohols to ketones or aldehydes catalyzed by anthraqui-none under irradiation at 430e440 nm at room temperature, using DMSO as an oxidant without acti-vated agent. Key parameters, including irradiating wave-length, reaction medium and photocatalyst, are investigated. According this procedure, a variety of alcohols are oxidized to the corresponding ketones or aldehydes in satisfactory yields. This protocol features transition metal free and mild reaction conditions. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

共 39 条

[1] Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4 nanoparticles [J].

Abinaya, R. ;

Mani Rahulan, K. ;

Srinath, S. ;

Rahman, Abdul ;

Divya, P. ;

Balasubramaniam, K. K. ;

Sridhar, R. ;

Baskar, B. .

GREEN CHEMISTRY, 2021, 23 (16) :5990-6007

[2] Bioinspired o-Naphthoquinone-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones [J].

Baek, Jisun ;

Si, Tengda ;

Kim, Hun Young ;

Oh, Kyungsoo .

ORGANIC LETTERS, 2022, 24 (27) :4982-4986

[3] Oxidation of secondary alcohols using solid-supported hypervalent iodine catalysts [J].

Ballaschk, Frederic ;

Kirsch, Stefan F. .

GREEN CHEMISTRY, 2019, 21 (21) :5896-5903

[4] Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds [J].

Cannalire, Rolando ;

Pelliccia, Sveva ;

Sancineto, Luca ;

Novellino, Ettore ;

Tron, Gian Cesare ;

Giustiniano, Mariateresa .

CHEMICAL SOCIETY REVIEWS, 2021, 50 (02) :766-897

[5] Large-scale oxidations in the pharmaceutical industry [J].

Caron, Stephane ;

Dugger, Robert W. ;

Ruggeri, Sally Gut ;

Ragan, John A. ;

Ripin, David H. Brown .

CHEMICAL REVIEWS, 2006, 106 (07) :2943-2989

[6] Bimolecular photoreduction of aromatic sulfoxides [J].

Cubbage, JW ;

Tetzlaff, TA ;

Groundwater, H ;

McCulla, RD ;

Nag, M ;

Jenks, WS .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8621-8628

[7] Visible light mediated chemo-selective oxidation of benzylic alcohols [J].

Devari, Shekaraiah ;

Rizvi, Masood Ahmad ;

Shah, Bhahwal Ali .

TETRAHEDRON LETTERS, 2016, 57 (30) :3294-3297

[8] Integration of Earth-Abundant Photosensitizers and Catalysts in Metal-Organic Frameworks Enhances Photocatalytic Aerobic Oxidation [J].

Feng, Xuanyu ;

Pi, Yunhong ;

Song, Yang ;

Xu, Ziwan ;

Li, Zhong ;

Lin, Wenbin .

ACS CATALYSIS, 2021, 11 (03) :1024-1032

[9] Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols [J].

Fuse, Hiromu ;

Mitsunuma, Harunobu ;

Kanai, Motomu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (09) :4493-4499

[10] Metal-Directed Self-Assembly of {Ti8L2} Cluster-Based Coordination Polymers with Enhanced Photocatalytic Alcohol Oxidation Activity [J].

Han, Er-Meng ;

Yu, Wei-Dong ;

Yan, Jun ;

Yi, Xiao-Yi ;

Liu, Chao .

INORGANIC CHEMISTRY, 2022, 61 (02) :923-930

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