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

doi:10.6023/cjoc202008027

Abstract

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

Cite this article

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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Fig. & Tab. 81

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

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

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

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

Scheme 4. Enantioselective synthesis of nicotine via iodine-catalyzed

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

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

Scheme 7. Iodine-mediated HLF-type cyclization reactions

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

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

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

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

Scheme 12. Synthesis of α-dicarbonylsulfoximine derivatives

Scheme 13. General catalytic strategies of I2/DMSO

Scheme 14. Construction of heterocyclic molecules via different cycloaddition formals

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 35. I2/Peroxide-catalyzed oxidative coupling reaction

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

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

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

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

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

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

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

Scheme 43. Iodine-mediated oxidative intramolecular amination of anilines

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

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

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

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

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

Scheme 49. Iodine-mediated tandem cyclization and oxidation reaction

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

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

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

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

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

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

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

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

Scheme 58. Stereoselective synthesis of trans-aziridines

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

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

Scheme 61. Electrocatalytic intermolecular cross-coupling reaction reactions

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

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

Scheme 64. I2/peroxide-catalyzed synthesis of indolizines

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

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

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

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

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

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

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

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

Scheme 73. Iodine-catalyzed diastereoselective cyclopropanation

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

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

Scheme 76. Halogenations of substituted 2-alkylquinoline with iodine

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

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

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

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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分子碘催化氧化C(sp3)—H功能化反应的研究进展