Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives

doi:10.6023/A25020057

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (7): 773-802.DOI: 10.6023/A25020057 Previous Articles

Review

光诱导醇的含氧衍生物的脱氧/功能化反应的研究进展

赵瑜^a^,^*(), 邢彤彤^a, 段玉荣^a, 赵全庆^b^,^*()

^a 延安大学化学与化工学院陕西化学反应工程重点实验室陕西延安 716000
^b 江苏海洋大学江苏省海洋药物活性分子筛选重点实验室药学院江苏连云港 222005

投稿日期:2025-02-27 发布日期:2025-07-28
通讯作者: 赵瑜, 赵全庆

作者简介:

赵瑜, 延安大学, 讲师. 2011年本科毕业于咸阳师范学院, 同年考入河南大学化学学院攻读有机化学硕士, 导师为江智勇教授, 于2014年7月获得理学硕士学位. 2015年进入华中师范大学化学学院攻读博士, 导师为肖文精教授和陈加荣教授, 于2018年7月毕业获得有机化学博士学位. 2018年7月进入延安大学化学与化工学院, 从事教学科研工作. 2022年12月进入西北工业大学化工学院从事博后工作, 合作导师为张秋禹教授. 研究方向为自由基反应和光化学合成反应.

邢彤彤, 男, 汉族, 2002出生于陕西西安. 2024年本科毕业于延安大学, 同年考入延安大学有机化学专业攻读硕士学位, 导师为赵瑜博士. 研究方向为光化学反应促进C－C键的构建.

段玉荣, 女, 汉族, 1998出生于陕西榆林. 2021年本科毕业于商洛学院, 同年考入延安大学有机化学专业攻读硕士学位, 导师为赵瑜博士. 研究方向为光化学反应促进C－C键的构建.赵全庆, 江苏海洋大学, 副教授. 2014年本科毕业于铜仁学院, 同年考入华中师范大学攻读有机化学硕士学位, 于2020年硕博连读获得博士学位, 导师为肖文精教授和陈加荣教授. 之后, 在德国雷根斯堡大学从事博士后研究, 导师为Oliver Reiser教授. 2023年2月入职江苏海洋大学药学院, 从事教学科研工作. 研究方向为绿色有机合成、药物中间体合成及自由基化学.

赵全庆, 江苏海洋大学, 副教授. 2014年本科毕业于铜仁学院, 同年考入华中师范大学攻读有机化学硕士学位, 于2020年硕博连读获得博士学位, 导师为肖文精教授和陈加荣教授. 之后, 在德国雷根斯堡大学从事博士后研究, 导师为Oliver Reiser教授. 2023年2月入职江苏海洋大学药学院, 从事教学科研工作. 研究方向为绿色有机合成、药物中间体合成及自由基化学.

基金资助:
国家自然科学基金(22161047); 国家自然科学基金(22301109); 江苏海洋大学人才引进项目(KQ23065); 连云港市海燕计划(KK24005)

Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives

Yu Zhao^a^,^*(), Tongtong Xing^a, Yurong Duan^a, Quanqing Zhao^b^,^*()

^a College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan’an University, Yan’an 716000, Shaanxi Province, China
^b Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, College of Pharmacy, Jiangsu Ocean University, Lianyungang 222005, Jiangsu Province, China

Received:2025-02-27 Published:2025-07-28
Contact: Yu Zhao, Quanqing Zhao
Supported by:
National Natural Science Foundation of China(22161047); National Natural Science Foundation of China(22301109); Research Funds for Talent Introduction of Jiangsu Ocean University(KQ23065); Lianyungang Haiyan Project(KK24005)

Alcohols are one of the most widespread existent in nature, and one of promising chemical feedstocks, due to their cheap and easy availability. Half a century ago, the Barton-McCombie deoxygenation was discovered, and continued to be improved by organic synthetic chemists, becoming an important and rather broad fields in modern organic chemistry. In the last decade, visible-light-driven photoredox catalysis is a powerful tool in organic synthesis, and can realize a good deal of chemical transformations, because of its milder reaction condition, functional group tolerance, high efficiency and environmental-friendly characteristics. It has been reported direct deoxygenation of alcohol in the previous literatures, including the photochemical reactions and metal-transition catalytic systems. Herein, we summarized and discussed some significant advances since in 2014, about the deoxygenative functionalization of alcohol derivatives in photochemical synthetic reactions. And oxygen-containing derivatives of alcohol mainly includes carboxylic esters, oxalic esters, thiocarbonates and their derivatives, ethers and others. In this minireview, in terms of their structural properties, we went to classify and introduce the catalytic modes and mechanisms of deoxygenation, reaction universalities, advantages and shortcomings. In these advances, the oxygen-containing derivatives of alcohol could proceed single electron oxidation and reduction processes, hydrogen atom transfer (HAT), as well as radical addition process, as to assist the C—O bond cleavage to yield the key alkyl radical intermediates, subsequent functionalization to construct the newly C—C, C—N, C—O, C—S, C—X (halo) and C—B bonds. In addition, we also outlooked the challenges and opportunities in the field of deoxygenation of alcohols, and the application prospects of some compounds containing the hydroxy group in the future was discussed as well.

Key words: deoxygenation of alcohol, photochemical reactions, oxygen-containing derivatives of alcohol, deoxygenative functionalization

Cite this article

Yu Zhao, Tongtong Xing, Yurong Duan, Quanqing Zhao. Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives[J]. Acta Chimica Sinica, 2025, 83(7): 773-802.

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Fig. & Tab. 60

Scheme 1. Reaction pathways of deoxygenation of alcohols

Scheme 2. Deoxygenation/reduction of benzoates

Scheme 3. Mechanism for deoxygenation/reduction of benzoates

Scheme 4. Deoxygenation/cyclization reactions of alcohol derivatives

Scheme 5. Deoxygenation/reduction of O-acetylbenzoins

Scheme 6. Asymmetric deoxygenative cyanation of benzyl alcohols by dual catalysis

Scheme 7. Modification of Lumefantrine

Scheme 8. Mechanism for asymmetric deoxygenative cyanation of benzyl alcohols

Scheme 9. Coupling reactions involving allenyl radical, allyl radical and benzyl radical

Scheme 10. Deoxygenation/azarylation of benzoates

Scheme 11. Synthesis of (hetero)aryl C-glycosides by photocatalysis and Ni catalysis

Scheme 12. Mechanism for synthesis of (hetero)aryl C-glycosides

Scheme 13. Deoxygenative C(sp3)—C(sp3) bond coupling reaction by photoredox and NHC catalysis

Scheme 14. Mechanism for deoxygenative C(sp3)—C(sp3) bond coupling reaction

Scheme 15. C(sp3)—C(sp3) coupling reaction mediated by visible light and phosphoric acid

Scheme 16. Deoxygenative alkylation, allylation and alkenylation of oxalic ester

Scheme 17. Deoxygenative radical addition reactions of alkyl substituted oxalate

Scheme 18. Deoxygenative radical addition reactions of alkyl substituted oxalate

Scheme 19. Deoxygenative (aza)arylation of alkyl substituted oxalic acid

Scheme 20. Mechanism for deoxygenative (aza)arylation of alkyl substituted oxalic acid

Scheme 21. Deoxygenative azarylation of alkyl substituted oxalic acid and their salt

Scheme 22. Multicomponent radical reations via photoredox catalysis and Ni catalysis

Scheme 23. Visible light induced C(sp3)—C(sp) coupling reaction of alkyl substituted oxalic salt

Scheme 24. Ritter-type amination of oxalic acid monoalkyl ester

Scheme 25. Visible-light-driven deoxygenative halogenation of alkyl substituted oxalic acids and their salts

Scheme 26. Mechanism for deoxygenative fluorination of alkyl substituted oxalic acid and their salts

Scheme 27. Deoxygenative borylation of alcohol derivatives

Scheme 28. Mechanism for deoxygenative borylation of alcohol derivatives

Scheme 29. Visible light-driven deoxydisulfuration of alcohols

Scheme 30. Photo and copper dual catalysis for synthesis of cyano-allenes

Scheme 31. Photocatalytic deoxygenative reduction of O-thiocarbamates

Scheme 32. Ni/photoredox catalyzed deoxygenative C(sp3)—C(sp2) cross-coupling reactions

Scheme 33. Photoinduced deoxygenative borylations of aliphatic alcohols

Scheme 34. Mechanism for photoinduced deoxygenative borylations of aliphatic alcohols

Scheme 35. Photo and copper promoted deoxygenative trifluoromethylation of O-alkyl thiocarbonates

Scheme 36. Copper catalyzed deoxygenative difluoromethylation of alcohol

Scheme 37. Visible-light-induced site-selective alkylation of pyridine

Scheme 38. Mechanism for site-selective alkylation of pyridine

Scheme 39. Selective deoxygenative radical addition reaction of alcohols

Scheme 40. Mechanism for selective deoxygenative radical addition reaction of alcohols

Scheme 41. Deoxygenative gem-difluorovinylation of aliphatic alcohol

Scheme 42. Visible-light-induced alkylation of xanthonate with electron withdrawing alkenes and arenes

Scheme 43. Mechanism for radical addition of xanthonate with imine

Scheme 44. Visible light-induce the synthesis of polysubstituted fatty aldehyde

Scheme 45. Mechanistic studies

Scheme 46. Methanism for the synthesis of polysubstituted fatty aldehyde

Scheme 47. Synergistic catalysis for trifluoromethylthiolation of tertiary ethers

Scheme 48. Mechanism for trifluoromethylthiolation of tertiary ethers

Scheme 49. Site-selective radical fluorination of tertiary ethers

Scheme 50. Mechanism for site-selective fluorination of tertiary ethers

Scheme 51. Photoinduced C(sp3)—C(sp3) bond cross-coupling reaction

Scheme 52. Alkoxyl radical generation for C(sp3)—C(sp3) cleavage

Scheme 53. Alkoxyl radical generation for C(sp3)—C(sp3) cleavage and arylation and alkylation

Scheme 54. Synthetic application

Scheme 55. Mechanism for alkoxyl radical generation for C(sp3)—C(sp3) cleavage and arylation

Scheme 56. Visible-light-induced alkylation of phenyl glycinate and peptide

Scheme 57. Deoxygenation allylation (alkenylation) of alkoxyl radicals

Scheme 58. Mechanism for deoxygenation allylation (alkenylation) of alkoxyl radicals

Scheme 59. Deoxygenative domino reaction of N-hydroxyl imine

Scheme 60. Deoxygenative/ring-opening/alkynylation of N-hydroxyl imine

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光诱导醇的含氧衍生物的脱氧/功能化反应的研究进展

Recent Advances of Photoinduced Deoxygenative Functionalization of Alcohol Derivatives

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