分子碘催化氧化C(sp3)—H功能化反应的研究进展

doi:10.6023/cjoc202008027

摘要/Abstract

现代有机合成中, C—H功能化反应可以用于直接构建各种生物活性骨架以及增加目标分子结构的复杂性, 是对传统合成方法的有效补充, 其中惰性C(sp³)—H功能化长期以来是该领域的难点. 目前, 碘试剂已被确定为经济和生态上无害的过渡金属替代品, 在具有挑战性的C(sp³)—H功能化反应中已经取得了卓有成效的进展. 分子碘与高价芳基碘试剂、二甲基亚砜(DMSO)、过氧化物以及氧气等组合, 能够高效地催化不同反应类型的C(sp³)—H功能化反应, 在不同氧化体系下具有不同的反应特点和机制. 另外, 近年来, 过渡金属/分子碘协同催化以及含碘电化学催化等新型碘催化体系在C(sp³)—H功能化反应中也得到了前所未有的发展. 综述了2015年至今分子碘在不同氧化体系下催化的C(sp³)—H功能化反应, 希望能进一步了解分子碘的绿色催化体系, 为深入研究C(sp³)—H功能化反应提供帮助.

关键词: 分子碘, C(sp³)—H功能化, 氧化体系, 绿色化学, 电化学

In modern organic synthesis, C—H functionalization can be used to construct various bioactive skeletons quickly and directly, and increase the complexity of the target molecular structure, which becomes an effective supplement to the traditional methods. Among them, C(sp³)—H functionalization has long been a big challenge in this field. Molecular iodine has been identified as an economically and ecologically harmless transition metal substitute, and tremendous progress has been made in the challenging C(sp³)—H functionalization reaction recently. The molecular iodine-catalyzed C(sp³)—H functionalization reactions under different oxidation systems have different reaction characteristics and mechanisms. The combination of molecular iodine and hypervalent aryl iodanes, dimethyl sulfoxide (DMSO), peroxide and oxygen can efficiently catalyze the functionalization of C(sp³)—H with different mechanisms. Recently, transition-metal/iodine co-cataly- sis and iodine-containing electrochemical catalysis have also made unprecedented progress in C(sp³)—H functionalization reaction. Herein, the progress of C(sp³)—H functionalization catalyzed by iodine under different oxidation systems from 2015 to now is summarized. The research on the green catalytic system of molecular iodine in the C(sp³)—H functionalization reaction is summarized and prospected.

Key words: molecular iodine, C(sp³)—H functionalization, oxidation system, green chemistry, electrochemistry

引用此文

张露文, 何炜. 分子碘催化氧化C(sp³)—H功能化反应的研究进展[J]. 有机化学, 2021, 41(4): 1359-1395.

Luwen Zhang, Wei He. Research Progress in C(sp³)—H Functionalization Reaction via Molecular Iodine-Catalyzed Oxidation[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1359-1395.

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图/表 81

图1. 不同的C(sp3)—H键键能和不同氧化体系

Figure 1. Different C(sp3)—H bonds energy and different oxidation systems

图式1. 分子碘在霍夫曼-勒夫勒-弗赖伊塔格反应中的应用

Scheme 1. Application of molecular iodine in Hofmann-L?fler- Freytag reaction

图式2. 碘催化的霍夫曼-勒夫勒反应

Scheme 2. Iodine-catalyzed Hofmann-L?ffler reaction

图式3. 碘催化霍夫曼-勒夫勒反应机理

Scheme 3. Mechanism of iodine-catalyzed Hofmann-Lo?ffler reaction

图式4. 碘催化对映选择性地合成尼古丁衍生物

Scheme 4. Enantioselective synthesis of nicotine via iodine-catalyzed

图式5. 通过碘催化Ritter型胺化反应合成1,3-二胺化合物

Scheme 5. Synthesis of 1,3-diamine by iodine catalyzed Ritter- type amination

图式6. 碘催化下分子间自由基C(sp3)—H胺化反应

Scheme 6. Intermolecular radical C(sp3)—H amination under iodine catalysis

图式7. 碘介导HLF环化反应

Scheme 7. Iodine-mediated HLF-type cyclization reactions

图式8. PIDA/I2介导的三级胺α-和β-双C(sp3)—H键功能化反应

Scheme 8. PIDA/I2-mediated α- and β-C(sp 3)—H bond dual functionalization of tertiary amines

图式9. 碘催化手性4-咪唑啉酮的合成

Scheme 9. Iodine-catalyzed synthesis of chiral 4-imidazo- lidinones

图式10. 亚胺自由基传递的β-C—H胺化催化反应

Scheme 10. Catalytic β-C—H amination via an imidate radical relay

图式11. 通过亚胺自由基极性交叉串联的醇邻近位点双C—H功能化

Scheme 11. Vicinal, double C—H functionalization of alcohols via an imidate radical-polar crossover cascade

图式12. α-二羰基亚砜亚胺衍生物的合成

Scheme 12. Synthesis of α-dicarbonylsulfoximine derivatives

图式13. I2/DMSO的一般催化策略

Scheme 13. General catalytic strategies of I2/DMSO

图式14. 不同环加成形式构建杂环分子

Scheme 14. Construction of heterocyclic molecules via different cycloaddition formals

图式15. 6-碘-3-甲基硫咪唑[1,2-a]吡啶化合物的直接合成

Scheme 15. Direct synthesis of 6-iodo-3-methylthioimidazo- [1,2-a]pyridines

图式16. 碘促进无保护的苯胺与甲基酮的氧化交叉偶联反应

Scheme 16. Iodine-promoted oxidative cross-coupling of unprotected anilines with methyl ketones

图式17. I2/DMSO介导多取代吡喃[3,2-c]苯并吡喃-2,5-二酮、α-酮酰胺和2-酰基噁唑的合成

Scheme 17. Synthesis of polysubstituted pyrano[3,2- c]chromene-2,5-diones, α-ketoamides and 2-acyl-oxazoles via I 2/DMSO-mediated

图式18. I2/DMSO介导1,2,4-三唑并[4,3-a]吡啶化合物的合成

Scheme 18. Synthesis of 1,2,4-triazolo[4,3-a]pyridines via I2/DMSO-mediated

图式19. 碘催化一锅法合成喹喔啉衍生物

Scheme 19. Iodine-catalyzed synthesis of quinoxaline derivatives via one-pot method

图式20. 分子碘促进由2'-氨基-β-酮酯高效合成吲哚醌

Scheme 20. Molecular iodine promoted efficient construction of isatins 2'-amino-β-ketoesters

图式21. 碘催化酮的α-羟基化和环己酮的多次氧合和脱氢芳构化

Scheme 21. I2-catalyzed α-hydroxylation of ketones and multiple oxygenation and dehydrogenative aromatization of cyclohexanone

图式22. I2/DMSO促进C(sp3)—H功能化合成α-酮酰胺

Scheme 22. I2/DMSO-promoted C(sp3)—H functionalization to synthesize α-ketoamides

图式23. I2/DMSO催化喹唑啉和C-4磺化吡唑类化合物的合成

Scheme 23. I2/DMSO-catalyzed synthesis of quinazolinones and C-4 sulfenylated pyrazoles

图式24. 碘介导羰基化合物和吡唑酮的区域选择性C—H磺酰化反应

Scheme 24. Iodine-mediated regioselective C—H sulfenylation of carbonyl compounds and pyrazolones

图式25. 碘促进由1,2-二苄基砜和二糠基二硫合成硫代酰胺

Scheme 25. Iodine-promoted synthesis of thioamides from 1,2-dibenzyl-sulfane and difurfuryl disulfide

图式26. 碘介导3-酰基苯并噻二嗪1,1-二氧化物的合成

Scheme 26. Iodine-mediated synthesis of 3-acylbenzothiadi- azine 1,1-dioxides

图式27. I2/DMSO催化N,N'-二芳基邻苯二胺化合物的合成

Scheme 27. I2/DMSO-catalyzed synthesis of N,N'-diaryl-o-phenylenediamines

图式28. 在空气中碘催化芳基肼氢氯化物的重氮化反应

Scheme 28. Iodine-catalyzed diazenylation with arylhydrazine hydrochlorides in air

图式29. I2/DMSO促进2-杂芳基苯并噻唑、甲基酮和1,3,4-噁二唑化合物的合成

Scheme 29. I2/DMSO-promoted synthesis of 2-heteroaryl-benzothiazole, methanones and 1,3,4-oxadiazole scaffolds

图式30. I2/DMSO介导α-异丙烯基丙酮一步合成呋喃环

Scheme 30. One-step synthesis of furan rings from α-isopropylidene ketones mediated by I 2/DMSO

图式31. 分子碘促进直接脱氢合成α,β-不饱和键羰基化合物

Scheme 31. Direct dehydrogenation for the synthesis of α,β-unsaturated carbonyl compounds via iodine-promoted

图式32. I2/DMSO促进了苄基C(sp3)—H键氧化构建二酮化合物

Scheme 32. I2/DMSO-promoted oxidation of benzylic C(sp3)—H bonds to diketones

图式33. 碘催化1,3,4-噁二唑化合物的合成

Scheme 33. Iodine-catalyzed synthesis of 1,3,4-oxadiazoles

图式34. 由I2/过氧化物引发自由基的一般策略

Scheme 34. General strategies of radical initiation by I2/peroxide

图式35. I2/过氧化物催化氧化偶联反应

Scheme 35. I2/Peroxide-catalyzed oxidative coupling reaction

图式36. I2/过氧化物催化2,5-二取代噁唑的合成

Scheme 36. I2/peroxide-catalyzed synthesis of 2,5-disubstituted- oxazoles

图式37. 碘催化C(sp3)—H功能化合成喹喔啉和苯酰胺化合物

Scheme 37. Iodine-catalyzed synthesis of quinoxalines and ben- zamides via C(sp3)—H functionalization

图式38. 碘催化分子内选择性C(sp3)—N氧化偶联

Scheme 38. Iodine-catalyzed intramolecular selective oxidative C(sp3)—N coupling

图式39. 碘催化氮杂芳烃与苄基C(sp3)—H键的交叉脱氢偶联

Scheme 39. Iodine-catalyzed cross dehydrogenative coupling of azaarenes with benzylic C(sp3)—H bonds

图式40. 碘催化肼和胺的氧化偶联反应

Scheme 40. Iodine-catalyzed oxidative coupling reactions of hydrazones and amines

图式41. I2/过氧化物催化磺化吡唑、苯并噁嗪酮(喹唑啉酮)和α-羰基硒氰酸酯化合物的合成

Scheme 41. I2/peroxide-catalyzed synthesis of sulfonated pyrazoles, benzoxazinones (quinazolinones) and α-carbonyl

图式42. 碘/过氧化氢促进分子内氧化C—O键的形成

Scheme 42. Iodine/H2O2 promoted intramolecular oxidative C—O bond formation

图式43. 碘介导的苯胺分子内氧化胺化

Scheme 43. Iodine-mediated oxidative intramolecular amination of anilines

图式44. I2/TBHP催化2-氮杂芳基-苯并咪唑和苯并噻唑化合物的合成

Scheme 44. I2/TBHP-catalyzed synthesis of 2-azaarenylbenzi- midazoles and benzothiazoles

图式45. I2/TBHP催化1,2,5-三芳基-1H-咪唑和3-取代-3-氨基吲哚酮的合成

Scheme 45. I2/TBHP-catalyzed synthesis of 1,2,5-triaryl-1H- imidazoles and 3-substituted 3-aminooxindoles

图式46. I2/TBHP介导酮和甲苯化合物的氧化偶联反应

Scheme 46. I2/TBHP-mediated oxidative coupling of ketones and toluene derivatives

图式47. 碘催化烷烃分子内C—H胺化反应

Scheme 47. Intramoleclar C—H amination of alkanes catalyzed by iodine

图式48. I2/TBHP催化异氰化物与氨基双核化合物的氧化偶联反应

Scheme 48. I2/TBHP-mediated oxidative coupling of amino- based bisnucleophiles and isocyanides

图式49. 碘介导串联环化和氧化反应

Scheme 49. Iodine-mediated tandem cyclization and oxidation reaction

图式50. 通过分子氧和碘实现硝基烷烃与胺亲核试剂的氧化酰胺化反应

Scheme 50. Oxidative amidation of nitroalkanes with amine nucleophiles by molecular oxygen and iodine

图式51. 碘催化2-吲哚酮和烯烃的直接烯烃化反应

Scheme 51. Iodine catalyzed direct olefination of 2-oxindoles and alkenes

图式52. 有氧下分子碘催化环己酮与2-氨基嘧啶或2-氨基吡啶α,β-二胺化

Scheme 52. Molecular iodine catalyzed aerobic α,β-diamination of cyclohexanones with 2-aminopyrimidine or 2-aminopyridines

图式53. 碘催化的光氧化分子间C—H/C—H偶联反应

Scheme 53. A photo-oxidative intermolecular C—H/C—H coupling reaction via iodine-catalyzed

图式54. 有氧条件下可见光介导碘催化α-亚甲基酮的α-羟基化

Scheme 54. Visible-light-mediated iodine-catalyzed α-hydroxy- lation of α-methylene ketones under aerobic conditions

图式55. 有氧条件下碘催化脱氢芳构化合成苯并唑和苯并嗪化合物

Scheme 55. Iodine-catalyzed convergent aerobic dehydroaromatization toward benzazoles and benzazines

图式56. nBu4NI催化分子间C—X交叉偶联反应

Scheme 56. nBu4NI-catalyzed intermolecular C—X cross-coupling reactions

图式57. KI-TBHP体系促进C(sp3)—H键功能化反应

Scheme 57. KI-TBHP-promoted C(sp3)—H bond functionalization

图式58. 反式氮杂环丙烷的立体选择性合成

Scheme 58. Stereoselective synthesis of trans-aziridines

图式59. NIS/TBHP介导稠合环咪唑类衍生物的合成

Scheme 59. NIS/TBHP-mediated synthesis of fused imidazole-containing ring systems

图式60. 酮类化合物的电化学氧化α-C—H功能化

Scheme 60. Electrochemically oxidative α-C—H functionalization of ketones

图式61. 电催化分子间交叉偶联反应

Scheme 61. Electrocatalytic intermolecular cross-coupling reaction reactions

图式62. N-羟基邻苯二甲酰亚胺介导的甲基杂环化合物的电化学碘化反应

Scheme 62. N-Hydroxyphthalimide-mediated electrochemical iodination of methylarenes

图式63. β-氨基芳基酮的脱氢环化电化学合成三取代的2-噁唑啉反应

Scheme 63. Electrosynthesis of trisubstituted 2-oxazolines via dehydrogenative cyclization of β-amino arylketones

图式64. I2/过氧化物催化吲嗪化合物的合成

Scheme 64. I2/peroxide-catalyzed synthesis of indolizines

图式65. 以甲基芳烃为酰基供体的亚砜亚胺氧化酰基化反应

Scheme 65. Oxidative acylation of sulfoximines with methyl- arenes as acyl donor

图式66. 碘和金属共同催化构建杂环

Scheme 66. Cooperative iodine and metal catalysis for construction of heterocyclic

图式67. 碘催化邻烷基芳烃有氧氧化为2H-吲哚化合物

Scheme 67. Iodine-catalyzed aerobic oxidation of o-alkyl- azoarenes to 2H-indazoles

图式68. 铁/碘催化咪唑并[1,2-a]吡啶衍生物的合成

Scheme 68. Iron/iodine-catalyzed synthesis of imidazo[1,2-a]- pyridines

图式69. 铜催化一锅合成2-芳基硫代色烯酮: 原位回收副产物(KI)作为有用试剂

Scheme 69. Copper-catalyzed one-pot synthesis of 2-arylthiochromenones: an in situ recycle of byproduct (KI) as useful reagent

图式70. 铜催化2-酰基二氢苯并噻吩和2-酰基苯并噻吩化合物的合成

Scheme 70. Copper-catalyzed synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes

图式71. 铜/碘共同催化1,3-二羰基化合物的C—C键裂解为1,2-二羰基化合物

Scheme 71. Copper/iodine-cocatalyzed C—C cleavage of 1,3-dicarbonyl compounds toward 1,2-dicarbonyl compounds

图式72. 碘催化分子内C(sp3)—H胺化反应

Scheme 72. Iodine-catalyzed intramolecular C(sp3)—H amination

图式73. 碘催化非对映选择性环丙基化反应

Scheme 73. Iodine-catalyzed diastereoselective cyclopropanation

图式74. 碘和可见光催化苯乙烯分子间环丙化反应

Scheme 74. Iodine and visible light catalyzed intermolecular cyclopropanation of styrenes

图式75. 碘催化氧化C—C和C—N键合成吲哚嗪类化合物

Scheme 75. Iodine-catalyzed synthesis of indolizines through oxidative C—C and C—N bond formations

图式76. 碘取代的2-烷基喹啉的卤代反应

Scheme 76. Halogenations of substituted 2-alkylquinoline with iodine

图式77. 分子碘介导的α-C—H氧化吡咯烷酮合成N,O-乙酰化合物

Scheme 77. Iodine-mediated α-C—H oxidation of pyrrolidines to N,O-acetals

图式78. 碘介导由N-烷基哌嗪一锅合成2-(哌嗪-1-)吡嗪衍生物

Scheme 78. Iodine-mediated one-pot synthesis of 2-(piperazin-1-yl)pyrazine derivatives from N-alkyl piperazines

图式79. 碘催化2α-位的2,3-二取代吲哚与氯胺盐的C—H酰胺化和亚胺化

Scheme 79. Iodine-catalyzed C—H amidation and imination at the 2α-position of 2,3-disubstituted indoles with chloramine salts

图式80. I2/K2S2O8介导1,3,5-三嗪衍生物的合成

Scheme 80. I2/K2S2O8-mediated synthesis of substituted 1,3,5-triazines

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分子碘催化氧化C(sp³)—H功能化反应的研究进展

Research Progress in C(sp³)—H Functionalization Reaction via Molecular Iodine-Catalyzed Oxidation

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