可见光促进高价碘(III)试剂参与反应的研究进展

doi:10.6023/cjoc202305022

有机化学 ›› 2023, Vol. 43 ›› Issue (12): 4106-4140.DOI: 10.6023/cjoc202305022 上一篇下一篇

综述与进展

可见光促进高价碘(III)试剂参与反应的研究进展

赵瑜^a^,^b^,^*(), 段玉荣^b, 史时辉^b, 白育斌^b, 黄亮珠^b, 杨晓军^b, 张琰图^b, 冯彬^c^,^*(), 张建波^a^,^*(), 张秋禹^a^,^*()

a 西北工业大学化学与化工学院西安市功能有机多孔材料重点实验室西安 710129
b 延安大学化学与化工学院陕西省化学反应工程重点实验室陕西延安 716000
c 百色学院化学与环境工程学院广西百色 533000

收稿日期:2023-05-17 修回日期:2023-07-30 发布日期:2023-08-22
基金资助:
国家自然科学基金(22161047); 陕西省科技计划(2019JM-516); 延安大学博士科研启动基金(YDBK2018-30)

Recent Advances of Hypervalent Iodine(III) Reagents upon Visible Light Irradiation

Yu Zhao^a^,^b,*(), Yurong Duan^b, Shihui Shi^b, Yubin Bai^b, Liangzhu Huang^b, Xiaojun Yang^b, Yantu Zhang^b, Bin Feng^c,*(), Jianbo Zhang^a,*(), Qiuyu Zhang^a,*()

a Xi'an Key Laboratory of Functional Organic Porous Materials, School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an 710129
b College of Chemistry and Chemical Engineeringt, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Yan'an, Shaanxi 716000
c College of Chemistry and Environment Engineering, Baise University, Baise, Guangxi 533000

Received:2023-05-17 Revised:2023-07-30 Published:2023-08-22
Contact: *E-mail: zhaoyyau@163.com;FB_BSUC@163.com;zhangjb@nwpu.edu.cn;qyzhang@nwpu.edu.cn
Supported by:
National Natural Science Foundation of China(22161047); Science and Technology Plan Project of Shaanxi Province(2019JM-516); Research Fund for the Doctoral Program of Yan'an University(YDBK2018-30)

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摘要/Abstract

近几十年来, 高价碘试剂受到有机合成化学工作者的关注, 并被广泛应用于有机合成反应中. 相较于强氧化性的五价碘试剂, 三价的高价碘试剂呈现出弱氧化性, 更符合绿色、环境友好的特点. 在过去十几年, 可见光诱导光致氧化还原催化反应作为一种强劲的有机合成新方法, 实现了许多重要的化学转化. 同时, 一些三价的碘试剂由于结构稳定、易获得的特点, 也被广泛应用于可见光促进的光化学反应中. 特别是苯并碘氧杂戊环(酮)类的三价碘试剂, 由于其优良的化学反应活性, 可以作为氧化剂、自由基受体、自由基前体和共催化剂, 从而参与到光化学反应中. 另外, 二醋酸碘苯及其衍生物在光催化的反应中也可以经历类似的反应途径. 三价碘试剂表现出的弱氧化性和优良的亲电性主要归结于其结构中含有高度极化的I—X键, 容易发生断裂. 主要总结并讨论了从2016年以来三价碘试剂参与光催化反应的研究进展, 根据不同类型的三价碘试剂参与的光化学反应, 就其反应特点和机理过程进行详细的讨论和陈述; 同时, 针对三价碘试剂将来的应用前景也进行了讨论.

关键词: 高价碘试剂, 可见光催化反应, 苯并碘氧杂戊环(酮)试剂, 二醋酸碘苯

Hypervalent iodine reagents have attracted much attention from organic synthetic chemists. Compared to the strong oxidizing iodine(V) reagents, iodine(III) reagents show a weaker oxidizing ability, which could meet green and environmentally-friendly properties. Over the past decade, visible-light-induced photoredox catalysis has merged as a powerful tool in organic synthetic methodology, and a rapid development was witnessed. It is worth noting that some iodine(III) reagents which are stable and easily available, have been widely utilized in visible light photocatalytic reactions. Particularly, benziodoxol(on)e reagents, due to their excellent activation properties, which can serve as oxidant, radical acceptor, radical precursor and co-catalyst in photocatalytic reactions, allow for many significant chemical transformations. Additionally, phenyliodine(III) diacetate and its derivatives can proceed similar pathway in photocatalytic reactions. These issues attribute to the highly polarized I—X bond of iodine reagents, leads to their oxidizing ability and superior electrophilicity. Herein, some significant advances since in 2016 are summaried and discussed in terms of chemical transformations and mechanisms of different iodine(III) reagents. In addition, the application prospects in the future are also discussed.

Key words: hypervalent iodine(III) reagents, photocatalytic reactions, benziodoxol(on)e reagents, phenyliodine(III) diacetate

引用此文

赵瑜, 段玉荣, 史时辉, 白育斌, 黄亮珠, 杨晓军, 张琰图, 冯彬, 张建波, 张秋禹. 可见光促进高价碘(III)试剂参与反应的研究进展[J]. 有机化学, 2023, 43(12): 4106-4140.

Yu Zhao, Yurong Duan, Shihui Shi, Yubin Bai, Liangzhu Huang, Xiaojun Yang, Yantu Zhang, Bin Feng, Jianbo Zhang, Qiuyu Zhang. Recent Advances of Hypervalent Iodine(III) Reagents upon Visible Light Irradiation[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4106-4140.

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图/表 74

Figure 1. Representative hypervalent iodine(III) reagents

Figure 2. Calculated I(III)—X bond dissociation energy for some common benziodoxol(on)e reagents

Scheme 1. Chemical transformation modes of hypevalent iodine(III) reagents

Scheme 2. ATRA reactions of unactivated alkenes catalyzed by TiO2

Scheme 3. Plausible mechanism of ATRA reaction

Scheme 4. Selective C—C cleavage of cycloalkanols enabled by Togni reagent I

Scheme 5. Mechanism for a selective C—C cleavage of cycloalkanols enabled by Togni reagent I

Scheme 6. Hydroaryldifluoromethylation of alkenes

Scheme 7. Possible mechanism for hydroaryldifluoromethylation

Scheme 8. A minisci C—H alkylation of N-heteroarenes mediated by photoredox catalysis and BI-OAc

Scheme 9. Mechanism for a minisci C—H alkylation of N-heteroarenes

Scheme 10. Deboronative cyanation of potassium alkyltrifluoroborates

Scheme 11. C(2) alkylation of pyridine N-oxides

Scheme 12. BIOAc accelerated C(3)—H alkylation of quinoxalin-2(1H)-ones

Scheme 13. Mechanism of a photocatalyst-free alkylation of quinoxalin-2(1H)-ones

Scheme 14. HIR promoted decarboxylative acylation of acrylamides

Scheme 15. Mechanism for the decarboxylative acylation of acrylamides

Scheme 16. BI-OH catalyzed decarboxylative acylation of phenyl propiolates

Scheme 17. Photoredox catalytic decarboxylative acylation/ring expansion of vinylcyclobutanols

Scheme 18. Alkyl radical addition/rearrangement of allylic cycloalkyl alcohols

Scheme 19. Oxidative decarboxylation of oxamic acids

Scheme 20. Oxidative decarboxylation of oxamic acids by PANI-g-C3N4-TiO2 composite

Scheme 21. Aromatic C—H amination mediated by photoredox catalysis and BI-OnBu

Scheme 22. Possible mechanism for aromatic C—H amination

Scheme 23. Decarboxylative alkynylation of carboxylic acid catalyzed by DCA

Scheme 24. Mechanism of decarboxylative alkynylation of carboxylic acid

Scheme 25. Decarboxylative alkynylation of C-terminal peptide

Scheme 26. Benzophenone catalyzed C(sp3)—H bond alkynylation and alkenylation of ethers and amides

Scheme 27. Mechanism for C(sp3)—H bond alkynylation and alkenylation of ethers and amides

Scheme 28. C—H alkynylation and deconstructive ring cleavage of heterocycles

Scheme 29. Generation and alkynylation of acyl radical via HAT process

Scheme 30. Plausible mechanism of alkynylation of acyl radical via HAT process

Scheme 31. Photoredox catalytic imino olefination, alkynylation and cyanation of olefins

Scheme 32. Remote cyanation and alkynylation of amides and amines

Scheme 33. Three-component amidyl radical addition of unactivated alkenes

Scheme 34. Reductive formation of iminyl radical from cyclic alkylketone oxime ether

Scheme 35. Mechanism for reductive formation of iminyl radical from cyclic alkylketone oxime ether

Scheme 36. Aryl-substituted EBX reagents promoted alkynylation reactions

Scheme 37. Alkoxyl radical enabled selective C—C bond cleavage and functionalization

Scheme 38. Proposal mechanism of selective C—C bond cleavage and alkynylation

Scheme 39. Generation of acyl radical via selective C—C bond cleavage and alkynylation

Scheme 40. Selective C(sp3)—C(sp3) cleavage/alkynylation of cycloalkylamides

Scheme 41. Mechanism for selective C(sp3)—C(sp3) cleavage/alkynylation of cycloalkylamides

Scheme 42. Enantioselective decarboxylative α-alkynylation of β-ketocarbonyls

Scheme 43. Proposed two-catalytic cycles for enantioselective alkynylation alkynylation

Scheme 44. Photocatalytic cyanation of tertiary amines and carboxylic acids

Scheme 45. Mechanism for the decarboxylative cyanation and alkynylation reactions

Scheme 46. Photocatalytic selective C—H bond azidation

Scheme 47. [Cu(dap)2]Cl promoted azidation reactions of styrenes

Scheme 48. Photocatalytic additions of 1-sulfoximidoyl-1,2-benziodoxoles to styrenes

Scheme 49. Photoredox catalytic nitrooxylation of oxindoles

Scheme 50. Radical-mediate selective β-H amination

Scheme 51. Radical-mediate selective β-H amination and dihalogenation

Scheme 52. Photocatalytic selective sulfoximidation of benzylic C—H bonds

Scheme 53. Photocatalytic oxy-sulfoximidation of styrenes

Scheme 54. Alkylation and trifluoromethylation and perfluoroalkylation of (hetero)arenes

Scheme 55. Regioselective C(3)—H trifluoromethylation of 2H-indazole

Scheme 56. Hydrodifluoromethylation of alkenes assisted by PIDA

Scheme 57. Mechanism for hydrodifluoromethylation of alke- nes assisted by PIDA

Scheme 58. Oxidative α-sulfyl alkylation of unactivated alkenes

Scheme 59. Mechanism for oxidative α-sulfyl alkylation of unactivated alkenes

Scheme 60. Oxidative alkylarylation of N-aryl benzoyl acrylamides

Scheme 61. Photoredox catalytic decarboxylative alkyl radical cascade reaction

Scheme 62. Mechanism for photoredox catalytic decarboxylative alkyl radical cascade reaction

Scheme 63. Diastereoselective radical hydroacylation of electron-deficient alkenes

Scheme 64. Decarboxylative acyl radical cascade reaction assisted by PIDA

Scheme 65. Thioacetalization of aldehydes assisted by HIR

Scheme 66. Mechanism for thioacetalization of aldehydes assisted by HIR

Scheme 67. Radical pentafluorosulfanylphenylation of styrenes

Scheme 68. Mechanism for radical pentafluorosulfanylphenylation of styrenes

Scheme 69. Photoredox catalytic arylation of phosphine

Scheme 70. Mechanism for photoredox catalytic arylation of phosphine

Scheme 71. Three-component fluoro sulfomidation of styrenes

Scheme 72. Mechanism for three-component fluoro sulfomidation of styrenes

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可见光促进高价碘(III)试剂参与反应的研究进展

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