光诱导醇的含氧衍生物的脱氧/功能化反应的研究进展

doi:10.6023/A25020057

化学学报 ›› 2025, Vol. 83 ›› Issue (7): 773-802.DOI: 10.6023/A25020057 上一篇

综述

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)

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摘要/Abstract

醇类化合物广泛存在于自然界中, 其来源丰富, 是便宜易得的化工原料之一. 早在半个世纪前, Barton- McCombie脱氧反应就被发现, 是研究较为深远的一种醇的脱氧转化方法. 醇的脱氧化反应也是现代有机合成中非常重要的板块之一, 涉及的研究领域相当广泛. 近十几年来, 可见光驱动的氧化还原反应作为一种强劲的有机合成手段, 可以实现许多重要的化学转化, 其具有反应条件温和、官能团兼容性好、反应高效性和环境友好的特点. 对于醇的直接脱氧化反应, 之前已经有文献报道过, 包含可见光促进的光化学反应和过渡金属催化. 在此, 我们主要总结并讨论了从2014年以来, 醇的含氧衍生物, 包括羧酸酯、草酸酯、硫代碳酸酯及其衍生物、醚类和其他醇的含氧衍生物, 在光化学反应中进行的脱氧化/功能化反应的研究进展. 依据醇的含氧衍生物的结构特点进行分类, 详细介绍不同结构类型的醇的含氧衍生物的催化脱氧的反应模式、反应普适性和机理过程等. 展望了该领域所面临的挑战和机遇, 并对其他含羟基结构化合物的光化学脱氧反应具有一定的指导和启发意义.

关键词: 醇的脱氧化反应, 光化学反应, 醇的含氧衍生物, 脱氧化/功能化反应

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

引用此文

赵瑜, 邢彤彤, 段玉荣, 赵全庆. 光诱导醇的含氧衍生物的脱氧/功能化反应的研究进展[J]. 化学学报, 2025, 83(7): 773-802.

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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图/表 60

图式1. 醇的脱氧反应途径

Scheme 1. Reaction pathways of deoxygenation of alcohols

图式2. 芳基甲酸酯的脱氧/还原反应

Scheme 2. Deoxygenation/reduction of benzoates

图式3. 芳基甲酸酯的脱氧/还原反应的机理

Scheme 3. Mechanism for deoxygenation/reduction of benzoates

图式4. 醇的衍生物的脱氧/环化反应

Scheme 4. Deoxygenation/cyclization reactions of alcohol derivatives

图式5. 乙酰基取代的安息香衍生物的脱氧/还原

Scheme 5. Deoxygenation/reduction of O-acetylbenzoins

图式6. 双催化促进立体选择性苄醇的脱氧化/氰化反应

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

图式7. Lumefantrine的结构修饰

Scheme 7. Modification of Lumefantrine

图式8. 立体选择性苄醇的脱氧化/氰化反应机理

Scheme 8. Mechanism for asymmetric deoxygenative cyanation of benzyl alcohols

图式9. 联烯基自由基、烯丙基自由基和苄基自由基参与的偶联反应

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

图式10. 醇的羧酸酯衍生物的脱氧/氮杂芳基化反应

Scheme 10. Deoxygenation/azarylation of benzoates

图式11. 光催化与镍协同催化C-(杂)芳基取代糖苷的合成

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

图式12. C-(杂)芳基取代糖苷合成的机理

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

图式13. 可见光氧化还原催化与氮杂卡宾协同催化的脱氧C(sp3)—C(sp3)键的偶联反应

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

图式14. 双催化促进脱氧C(sp3)—C(sp3)键的偶联反应的机理

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

图式15. 可见光与磷酸促进的C(sp3)—C(sp3)偶联反应

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

图式16. 草酸酯的脱氧烷基化、烯丙基化和烯基化反应

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

图式17. 烷基取代草酸盐的脱氧/自由基加成反应

Scheme 17. Deoxygenative radical addition reactions of alkyl substituted oxalate

图式18. 烷基取代草酸盐的脱氧/自由基加成反应

Scheme 18. Deoxygenative radical addition reactions of alkyl substituted oxalate

图式19. 烷基取代草酸的芳(氮杂)基化反应

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

图式20. 烷基取代草酸的芳(氮杂)基化反应的机理

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

图式21. 烷基取代草酸和其盐的脱氧/氮杂芳基化反应

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

图式22. 光氧化还原催化与镍协同催化三组分的自由基反应

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

图式23. 可见光促进烷基取代草酸盐的C(sp3)—C(sp)偶联反应

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

图式24. 可见光驱动叔醇衍生物的Ritter类型的胺化反应

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

图式25. 可见光驱动烷基取代草酸盐的脱氧/卤化反应

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

图式26. 可见光驱动烷基取代草酸的脱氧/氟化的反应机理

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

图式27. 醇衍生物的脱氧/硼化反应

Scheme 27. Deoxygenative borylation of alcohol derivatives

图式28. 醇衍生物的脱氧/硼化反应的机理

Scheme 28. Mechanism for deoxygenative borylation of alcohol derivatives

图式29. 可见光驱动醇的脱氧/二硫化反应

Scheme 29. Visible light-driven deoxydisulfuration of alcohols

图式30. 光催化与铜协同促进氰基取代的联烯类化合物的合成

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

图式31. 光催化O-硫代氨基甲酸酯类化合物的脱氧/还原反应

Scheme 31. Photocatalytic deoxygenative reduction of O-thiocarbamates

图式32. 光催化与镍协同催化苄醇的脱氧/C(sp3)—C(sp2)的偶联反应

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

图式33. 可见光诱导的脂肪醇的脱氧/硼化反应

Scheme 33. Photoinduced deoxygenative borylations of aliphatic alcohols

图式34. 可见光诱导的脂肪醇的脱氧/硼化的反应机理

Scheme 34. Mechanism for photoinduced deoxygenative borylations of aliphatic alcohols

图式35. 可见光/铜协同促进O-烷基-硫代碳酸酯的脱氧/三氟甲基化反应

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

图式36. 铜催化醇的脱氧/二氟甲基化反应

Scheme 36. Copper catalyzed deoxygenative difluoromethylation of alcohol

图式37. 可见光促进吡啶的位点选择性烷基化反应

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

图式38. 吡啶的位点选择性烷基化反应机理

Scheme 38. Mechanism for site-selective alkylation of pyridine

图式39. 醇的选择性脱氧/自由基加成反应

Scheme 39. Selective deoxygenative radical addition reaction of alcohols

图式40. 醇的选择性脱氧/自由基加成反应的机理

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

图式41. 脂肪醇的脱氧/二氟乙烯化反应

Scheme 41. Deoxygenative gem-difluorovinylation of aliphatic alcohol

图式42. 可见光诱导O-烷基黄原酸盐与缺电子烯烃和芳烃的烷基化反应

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

图式43. O-烷基黄原酸盐与N-磺酰基亚胺的自由基加成反应的机理

Scheme 43. Mechanism for radical addition of xanthonate with imine

图式44. 可见光诱导多取代脂肪醛的合成

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

图式45. 机理研究

Scheme 45. Mechanistic studies

图式46. 可见光诱导多取代醛的合成的反应机理

Scheme 46. Methanism for the synthesis of polysubstituted fatty aldehyde

图式47. 双催化策略促进三级醚的脱氧/硫三氟甲基化反应

Scheme 47. Synergistic catalysis for trifluoromethylthiolation of tertiary ethers

图式48. 双催化策略促进三级醚的脱氧/硫三氟甲基化反应的机理历程

Scheme 48. Mechanism for trifluoromethylthiolation of tertiary ethers

图式49. 三级醚的位点选择性的自由基脱氧/氟化反应

Scheme 49. Site-selective radical fluorination of tertiary ethers

图式50. 三级醚的位点选择性的脱氧/氟化反应的机理

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

图式51. 光促进C(sp3)—C(sp3)键的交叉偶联反应

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

图式52. 烷氧基自由基驱动的C(sp3)—C(sp3)键的断裂反应

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

图式53. 烷氧基自由基驱动的C(sp3)—C(sp3)键的断裂、芳基化和烷基化反应

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

图式54. 合成应用

Scheme 54. Synthetic application

图式55. 烷氧基自由基驱动C(sp3)—C(sp3)键的断裂、芳基化反应机理

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

图式56. 可见光促进苯甘氨酸和多肽的烷基化结构修饰

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

图式57. 可见光促进烷氧基自由基的脱氧/烯丙基化(烯基化)反应

Scheme 57. Deoxygenation allylation (alkenylation) of alkoxyl radicals

图式58. 可见光促进烷氧基自由基的脱氧/烯丙基化(烯基化)反应机理

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

图式59. N-羟基亚胺的脱羟基多米诺反应

Scheme 59. Deoxygenative domino reaction of N-hydroxyl imine

图式60. N-羟基亚胺的脱羟基/开环/炔基化反应

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

参考文献 14

[14]	(b) Lu F.-D.; Lu L.-Q.; He G.-F.; Bai J.-C.; Xiao W.-J. J. Am. Chem. Soc. 2021, 143, 4168. pmid: 32157891
	(c) Yu X.-Y.; Chen J.; Chen H.-W.; Xiao W.-J.; Chen J.-R. Org. Lett. 2020, 22, 2333. doi: 10.1021/acs.orglett.0c00532 pmid: 32157891
[15]	Kolusu S. R. N.; Nappi M. Chem. Sci. 2022, 13, 6982.
[16]	Wei Y.; Ben-zvi B.; Diao T. Angew. Chem. Int. Ed. 2021, 60, 9433.
[17]	Li Z.; Wang L.; Zeng T.; Huang Z.; Song S.; Qi X.; Zhu J. ACS Catal. 2024, 14, 9496.
[18]	Wang Y.; Zhang S.; Zeng K.; Zhang P.; Song X.; Chen T. G.; Xia G. Nat. Commun. 2024, 15, 6745. doi: 10.1038/s41467-024-50897-7 pmid: 39117625
[19]	Barton D. H. R.; Crich D. J. Chem. Soc., Perkin Trans. 1 1986, 1603.
[20]	(a) Lackner G. L.; Quasdorf K. W.; Overman L. E. J. Am. Chem. Soc. 2013, 135, 15342.
	(b) Lackner G. L.; Quasdorf K. W.; Pratsch G.; Overman L. E. J. Org. Chem. 2015, 80, 6012.
[21]	Nawrat C. C.; Jamison C. R.; Slutskyy Y.; MacMillan D. W. C.; Overman L. E. J. Am. Chem. Soc. 2015, 137, 11270.
[22]	Wang Q.; Yue L.; Bao Y.; Wang Y.; Kang D.; Gao Y.; Yuan Z. J. Org. Chem. 2022, 87, 8237.
[23]	Zhang X.; MacMillan D. W. C. J. Am. Chem. Soc. 2016, 138, 13862.
[24]	(a) Pitre S. P.; Muuronen M.; Fishman D. A.; Overman L. E. ACS Catal. 2019, 9, 3413.
	(b) Liu G.; Mu X.; Tian M.; Wang W.; Zou C.; Chen Y.; Yu M. Eur. J. Org. Chem. 2023, 26, e202201491.
[25]	(a) Guo L.; Song F.; Zhu S.; Li H.; Chu L. Nat. Commun. 2018, 9, 4543.
	(b) Li H.; Guo L.; Feng X.; Huo L.; Zhu S.; Chu L. Chem. Sci. 2020, 11, 4904.
[26]	(a) Le Vaillant F.; Waser J. Chem. Sci. 2019, 10, 8909. doi: 10.1039/c9sc03033f pmid: 31762975
	(b) Amos S. G. E.; Waser J. Chimia 2022, 76, 312. pmid: 31762975
[27]	Li M.; Liu T.; Li J.; He H.; Dai H.; Xie J. J. Org. Chem. 2021, 86, 12386.
[1]	Hukumoto Y. Nature 1934, 134, 538.
[2]	Chheda J. N.; Dumesic J. A. Catal. Today 2007, 123, 59.
[3]	(a) Harrison I. T.; Harrison S. In Compendium of Organic Synthetic Methods, Wiley, Hoboken, New Jersey, 2006, pp. 329-356.
	(b) Harrison I. T.; Harrison S. In Compendium of Organic Synthetic Methods, Wiley, Hoboken, New Jersey, 2006, pp. 357-378.
[4]	(a) Barton D. H. R.; McCombie S. W. J. Chem. Soc., erkin Trans. 1. 1975, 1574.
	(b) Hartwig W. Tetrahedron 1983, 39, 2609.
	(c) Herrmann J. M.; König B. Eur. J. Org. Chem. 2013, 2013, 7017.
[5]	(a) McCombie S. W.; Motherwell W. B.; Tozer M. J. The Barton- McCombie Reaction, Wiley, Hoboken, New Jersey, 2012, pp. 161-591. pmid: 12735742
[28]	Amos S. G. E.; Cavalli D.; Le Vaillant F.; Waser J. Angew. Chem. Int. Ed. 2021, 60, 23827.
[29]	Kiyokawa K.; Watanabe T.; Fra L.; Kojima T.; Minakata S. J. Org. Chem. 2017, 82, 11711. doi: 10.1021/acs.joc.7b01202 pmid: 28603990
[30]	(a) Su J. Y.; Grunenfelder D. C.; Takeuchi K.; Reisman S. E. Org. Lett. 2018, 20, 4912.
	(b) Brioche J. Tetrahedron Lett. 2018, 59, 4387.
	(c) Gonzalez-Esguevillas M.; Miro J.; Jeffrey J. L.; MacMillan D. W. C. Tetrahedron 2019, 75, 4222.
[31]	Friese F. W.; Studer A. Angew. Chem. Int. Ed. 2019, 58, 9561.
[32]	Liu C.; Lin X.; An D.; Wang X.; Gao Q. Org. Chem. Front. 2024, 11, 358.
[33]	Liu Q.; Zheng J.; Zhang X.; Ma S. Nat. Commun. 2022, 13, 3302. doi: 10.1038/s41467-022-30655-3 pmid: 35676260
[34]	Chenneberg L.; Baralle A.; Daniel M.; Fensterbank L.; Goddard J. P.; Ollivier C. Adv. Synth. Catal. 2014, 356, 2756.
[35]	Vara B. A.; Patel N. R.; Molander G. A. ACS Catal. 2017, 7, 3955.
[36]	Wu J.; Bär R. M.; Guo L.; Noble A.; Aggarwal V. K. Angew. Chem. Int. Ed. 2019, 58, 18830.
[37]	Liu Z.-Y.; Cook S. P. Org. Lett. 2021, 23, 808.
[38]	Cai A.; Yan W.; Liu W. J. Am. Chem. Soc. 2021, 143, 9952.
[39]	Tan C. Y.; Kim M.; Park I.; Kim Y.; Hong S. Angew. Chem. Int. Ed. 2022, 61, e202213857.
[5]	(b) Chatgilialoglu C. Organosilanes in Radical Chemistry, John Wiley & Sons Ltd, Chichester, 2004, pp. 1-227. pmid: 12735742
	(c) Boivin J.; Jrad R.; Juge S.; Nguyen V. T. Org. Lett. 2003, 5, 1645. pmid: 12735742
	(d) Ueng S.-H.; Makhlouf-Brahmi M.; Derat E.; Fensterbank L.; Lacôte E.; Malacria M.; Curran D. P., J. Am. Chem. Soc. 2008, 130, 10082. pmid: 12735742
	(e) Ueng, S-H.; Fensterbank L.; Lacôte E.; Malacria M.; Curran D. P. Org. Lett. 2010, 12, 300. pmid: 12735742
	(f) Curran D. P.; Solovyev A.; Makhlouf-Brahmi M.; Fensterbank L.; Malacria M.; Lacôte E. Angew. Chem. Int. Ed. 2011, 50, 10294. pmid: 12735742
	(g) Boivin J.; Nguyen V. T. Beilstein J. Org. Chem. 2007, 3, 1. pmid: 12735742
[6]	Chenneberg L.; Ollivier C. Chimia 2016, 70, 67. doi: 10.2533/chimia.2016.67 pmid: 26931220
[7]	Recent advances for photoredox catalysis: (a) Prier C. K.; Rankic D. A.; MacMillan D. W. C. Chem. Rev. 2013, 113, 5322.
[40]	Guo H.-M.; Wu X. Nat. Commun. 2021, 12, 5365.
[41]	Xia G.-D.; He Y.-Y.; Zhang J.; Liu Z.-K.; Gao Y.; Hu X.-Q. Chem. Commun. 2022, 58, 6733.
[42]	(a) Guo H.-M.; He B.-Q.; Wu X. Org. Lett. 2022, 24, 3199.
	(b) Zhang W.; Ning S.; Li Y.; Wu X. Chem. Commun. 2022, 58, 12843.
	(c) Bao W.-H.; Wu X. J. Org. Chem. 2023, 88, 3975.
	(d) Xiong Y.; Zhang Q.; Zhang J.; Wu X. J. Org. Chem. 2024, 89, 3629.
	(e) Xiong Y.; Wu X. Org. Biomol. Chem. 2023, 21, 9316.
	(f) Li X.; Jiao Y.; Han L.; Sun J.; Zhang X. Org. Biomol. Chem. 2023, 21, 3330.
[43]	Murakami M.; Ishida N. Chem. Lett. 2017, 46, 1692.
[44]	Wu F.; Wang L.; Chen J.; Nicewicz D. A.; Huang Y. Angew. Chem. Int. Ed. 2018, 57, 2174.
[45]	Xu W.; Ma J.; Yuan X. A.; Dai J.; Xie J.; Zhu C. Angew. Chem. Int. Ed. 2018, 57, 10357.
[46]	Ma J.; Xu W.; Xie J. Sci. China Chem. 2020, 63, 187.
[7]	(b) Meggers E., Chem. Commun. 2015, 51, 3290.
	(c) Romero N. A. and Nicewicz D. A. Chem. Rev. 2016, 116, 10075.
	(d) Skubi K. L.; Blum T. R.; Yoon T. P. Chem. Rev. 2016, 116, 10035.
	(e) Huang H.; Jia K.; Chen Y. ACS Catal. 2016, 6, 4983.
	(f) Silvi M.; Melchiorre P. Nature. 2018, 554, 41.
	(g) Qiao B.; Jiang Z. ChemPhotoChem 2018, 2, 703.
	(h) Marzo L.; Pagire S. K.; Reiser O.; König B. Angew. Chem., Int. Ed. 2018, 57, 10034.
	(i) Yu X.-Y.; Chen J.-R.; Xiao W.-J. Chem. Rev. 2021, 121, 506.
	(j) Zhao Y.; Duan Y. R.; Shi S. H.; Bai Y. B.; Huang L. Z.; Yang X. J.; Zhang Y. T.; Feng B.; Zhang J. B.; Zhang Q. Y. Chin. J. Org. Chem. 2023, 43, 4106.
	(k) Zhao Q. Q.; Yan D. M.; Chen J. R.; Xiao W. J. Target in Heterocyclic Systems: Chemsitry and Properties, Italian Society of Chemistry, Roma, 2017, pp. 202-227.
[47]	Li Y.; Guo S.; Li Q.-H.; Zheng K. Nat. Commun. 2023, 14. 6225.
[48]	(a) Zhang J.; Li Y.; Zhang F.; Hu C.; Chen Y. Angew. Chem. Int. Ed. 2015, 55, 1872.
	(b) Zhang J.; Li Y.; Xu R.; Chen Y. Angew. Chem. In. Ed. 2017, 56, 12619.
[49]	Cong F.; Lv X.-Y.; Day C. S.; Martin R. J. Am. Chem. Soc. 2020, 142, 20594. doi: 10.1021/jacs.0c11172 pmid: 33252234
[50]	Gao Y.; Liu J.; Wei C.; Zhang K.; Song L.; Cai L. Nat. Commun. 2022, 13, 7450.
[51]	Han J. B.; Guo A.; Tang X. Y. Chem. Eur. J. 2019, 25, 2989.
[52]	Yao S.; Zhang K.; Zhou Q.-Q.; Zhao Y.; Shi D.-Q.; Xiao W.-J. Chem. Commun. 2018, 54, 8096.
[53]	(a) Jiang H.; Mao G.; Wu H.; An Q.; Zuo M.; Guo W.; Xu C.; Sun Z.; Chu W. Green Chem. 2019, 21, 5368.
	(b) Zhang M.; Yuan X. A.; Zhu C.; Xie J. Angew. Chem. Int. Ed. 2019, 58, 312.
	(c) Sun A. C.; McClain E. J.; Beatty J. W.; Stephenson C. R. J. Org. Lett. 2018, 20, 3487.
	(d) Zhao Y.; Chen J.-R.; Xiao W.-J. Org. Lett. 2017, 20, 224.
	(e) Zhao F.; Jiang F.; Wang X. Sci. China Chem. 2022, 65, 2231.
[7]	(l) Li K. K.; Long X. Y.; Huang Y.; Zhu S. F. Acta Chim. Sinica 2024, 82, 658 (in Chinese).
	(李康葵, 龙先扬, 黄岳, 祝诗发, 化学学报, 2024, 82, 658.) doi: 10.6023/A24030090
	(m) Gui C. M.; Zhou T. Y.; Wang H. F.; Yan Q. J.; Wang W.; Huang J.; Chen F. E. Chin. J. Org. Chem. 2023, 43, 2647 (in Chinese).
	(归春明, 周潼瑶, 王海峰, 严琼姣, 汪伟, 黄锦, 陈芬儿, 有机化学, 2023, 43, 2647.) doi: 10.6023/cjoc202303020
[8]	(a) Hu X.-Q.; Hou Y.-X.; Liu Z.-K.; Gao Y. Org. Chem. Front. 2020, 7, 2319. pmid: 32905246
	(b) Maddigan‐Wyatt J.; Hooper J. F. Adv. Synth. Catal. 2021, 363, 924. pmid: 32905246
	(c) Pan D.; Nie G.; Jiang S.; Li T.; Jin Z. Org. Chem. Front. 2020, 7, 2349. pmid: 32905246
	(d) Rossi-Ashton J. A.; Clarke A. K.; Unsworth W. P.; Taylor R. J. K. ACS Catal. 2020, 10, 7250. doi: 10.1021/acscatal.0c01923 pmid: 32905246
	(e) Shao X. Q.; Zheng Y.; Ramadoss V.; Tian L. F.; Wang Y. H. Org. Biomol. Chem. 2020, 18, 5994. pmid: 32905246
	(f) Mandal T.; Mallick S.; Islam M.; De Sarkar S. ACS Catal. 2024, 14, 13451. pmid: 32905246
	(g) Roy M.; Sardar B.; Mallick I.; Srimani D. Beilstein J. Org. Chem. 2024, 20, 1348. pmid: 32905246
[9]	Transition metal catalyzed the C—O bond activation: (a) Bisz E.; Szostak M. ChemSusChem 2017, 10, 3865.
	(b) Li X.; Hong X. J. Organomet. Chem. 2018, 864, 68.
	(c) Pound S. M.; Watson M. P. Chem. Commun. 2018, 54, 12286.
	(d) Hu W. Q.; Pan S.; Xu X. H.; Vicic D. A.; Qing F. L. Angew. Chem. Int. Ed. 2020, 59, 16076.
	(e) Zhou T.; Szostak M. Catal. Sci. Technol. 2020, 10, 5702.
	(f) Zhang S.-Q.; Hong X. Acc. Chem. Res. 2021, 54, 2158.
	(g) Diao H. Y.; Shi Z. J.; Liu F. Synlett 2021, 32, 1494.
	(h) Xu J.; Bercher O. P.; Talley M. R.; Watson M. P. ACS Catal. 2021, 11, 1604.
	(i) Villo P.; Shatskiy A.; Kärkäs M. D.; Lundberg H. Angew. Chem. Int. Ed. 2022, 62, e202211952.
	(j) Li P.; Zhang M.; Zhang L. Topics Curr. Chem. 2024, 382, 38.
	(k) Jiang N.-Q.; Ling M.-M.; Xiao L.-J.; Zhou Q.-L. Angew. Chem. Int. Ed. 2024, 366, 3829.
	(l) Li M.-M.; Zhang T.; Cheng L.; Xiao W.-G.; Ma J.-T.; Xiao L.-J.; Zhou Q.-L. Nat. Commun. 2023, 14, 3326.
	(m) Wang G.-Y.; Ge Z. L.; Ding K. L.; Wang X. M. Angew. Chem. Int. Ed. 2023, 21, e202307973.
	(n) Yuan F. Y.; Li C.; Luo M. M.; Zeng X. M. Acta Chim. Sinica 2023, 81, 456 (in Chinese).
	袁芳艳, 李超, 罗美明, 曾小明, 化学学报, 2023, 81, 456). doi: 10.6023/A23020048
	(o) Liu L. Q.; Zhang B.; Liu Y.; Zhao J. B.; Li T.; Zhao W. X. Chin. Chem. Lett. 2024, 35, 108631.
	(p) Lin L. L.; Zhou Y. Q.; Cao W. D.; Dong S. X.; Liu X. H.; Feng X. M. Sci. Sin. Chim. 2023, 53, 246.
[10]	Rackl D.; Kais V.; Kreitmeier P.; Reiser O. Beilstein J. Org. Chem. 2014, 10, 2157.
[11]	Rackl D.; Kais V.; Lutsker E.; Reiser O. Eur. J. Org. Chem. 2017, 2130.
[12]	Speckmeier E.; Padié C.; Zeitler K. Org. Lett. 2015, 17, 4818. doi: 10.1021/acs.orglett.5b02378 pmid: 26372674
[13]	Chen H. W.; Lu F. D.; Cheng Y.; Jia Y.; Lu L. Q.; Xiao W. J. Chin. J. Chem. 2020, 38, 1671.
[14]	(a) Lu F.-D.; Shu Z.-C.; He G.-F.; Bai J.-C.; Lu L.-Q.; Xiao W.-J. Org. Chem. Front. 2022, 9, 5259. pmid: 32157891

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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