高价碘试剂介导下的氧化重排反应

doi:10.6023/cjoc202206039

摘要/Abstract

在过去的40年间, 高价碘化学得到了迅猛发展, 受到了广大有机合成工作者的广泛关注. 高价碘试剂具有低毒、易制备、环境友好等优点, 可以参与多种类型的氧化偶联、官能团化及重排等多种类型的反应; 其中, 就高价碘试剂参与的氧化重排反应而言, 类型众多, 常见的反应包C—X重排(X=C, N, O), X—C重排(X=N, O, S, Si, I), I—X重排(X=O, N)以及sigmatropic重排. 对高价碘试剂参与的氧化重排反应进行了全面总结, 以方便读者了解该领域的相关研究进展.

关键词: 高价碘试剂, 氧化反应, 重排反应

During the past 40 years, hypervalent-iodine chemistry has developed rapidly and extensive attention has been received from many organic researchers. For their advantages of low toxicity, easy preparation and environmental benignity, hypervalent iodine reagents have been widely applied in various types of organic transformation including oxidative coupling, functionalization, and rearrangement reactions. Among them, there exist a series of oxidative rearrangement reactions, which can be classified into many types including C to X migration (X=C, N or O), X to C migration (X=N, O, S, Si or I), I to X migration (X=O or N) and sigmatropic rearrangement. This review comprehensively summarizes the oxidative rearrangement reactions enabled by hypervalent iodine reagents, providing convenience for organic readers to learn the progress of this research field.

Key words: hypervalent-iodine reagents, oxidative reaction, rearrangement reaction

引用此文

杨治芳, 程乙夫, 张蓓蓓, 董韵怡, 韩驰, 杜云飞. 高价碘试剂介导下的氧化重排反应[J]. 有机化学, 2022, 42(11): 3456-3505.

Zhifang Yang, Yifu Cheng, Beibei Zhang, Yunyi Dong, Chi Han, Yunfei Du. Oxidative Rearrangement Reactions Mediated by Hypervalent-Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3456-3505.

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图/表 145

Scheme 1. Difluorinated 1,2-phenyl migration mediated by PhIF2 generated in situ

Scheme 2. Different outcomes of reactions between HTIB with styrene derivatives

Scheme 3. 1,2-Aryl migration of chalcones and ketones mediated by HTIB or PhIO

Scheme 4. Mechanism of 1,2-phenyl migration of styrenes, chalcones and ketones

Scheme 5. 1,2-Aryl migratiom of styrenes or chalcones triggered by PIDA

Scheme 6. Mechanism of 1,2-migratiom of styrene mediated by PIDA

Scheme 7. Oxidative 1,2-migration of ketones mediated by PIDA or HMBI

Scheme 8. In situ generated hypervalent iodine species-mediated oxidative rearrangement of 1,1-disubstituted olefins

Scheme 9. PIDA-mediated oxidative 1,2-aryl shift of chalcones under acidic conditions

Scheme 10. Oxidative 1,2-aryl shift of cinnamic acids mediated by PIDA under acid condition

Scheme 11. Oxidative 1,2-aryl-migration of chalcones to gem-ditosyloxy ketones with HTIB

Scheme 12. Oxidative 1,2-alkylthio-migration of α,β-unsaturated amide to enaminones by employing PIDA

Scheme 13. 1,2-Aryl migration of 3-bromo-l-phenylpropynol mediated by stoichiometric amounts of I2 and HTIB or PIDA

Scheme 14. 1,2-Migration of 1-alkoxyallenes triggered by HTIB and the possible pathway

Scheme 15. 1,2-Migration of allenes mediated by HTIB and its control reaction by employing PIDA

Scheme 16. 1,2-Migration of non-terminal alkynes mediated by in situ formed phenyl(fluoro)iodonium triflate

Scheme 17. 1,2-Migration and possible pathway of trialkylamines mediated by phthalimide-containing I(III) reagent

Scheme 18. 1,2-Migration of flavonones to isoflavones with HTIB.

Scheme 19. 1,2-Aryl migration of chalcones to α-aryl ketones mediated by chiral hypervalent iodine reagent.

Scheme 20. 1,2-Shift of 1,1-disubstituted alkenes to α-arylated ketones mediated by catalytic chiral aryliodine

Scheme 21. 1,2-Shift of disubstituted olefins to tert-α-arylated aldehydes mediated by chiral iodine(III) reagent

Scheme 22. 1,2-Shift of arylketones with α-arylated esters mediated by the chiral iodine(III) reagent

Scheme 23. 1,2-Shift of allylic alcohols to α-arylated β-alkoxylated ketones mediated by in situ generated I(III)-species

Scheme 24. Asymmetric 1,2-shift of allylic alcohols to α-arylated β-alkoxylated ketones and mediated by in situ generated I(III)-species

Scheme 25. 1,2-Aryl migration of chalcones to isoflavones involving hypervalent iodine reagents

Scheme 26. 1,2-Shift of chalcones to isoflavone derivatives mediated by HTIB or PIDA under refluxing

Scheme 27. Cyclization/migration of 4-aryl-4-pentenoic acids to aryl-migrated lactones mediated by PIDA

Scheme 28. Cyclization/migration of enoic acids mediated by PIFA

Scheme 29. Cyclization/migration of 2-(1-arylvinyl)benzoic acids triggered by I(III) species originated in situ from the reaction of PhIO and alkyl alcohols

Scheme 30. Cyclization/migration of 4-aryl-4-pentenoic acids to azido lactones mediated by azido-containing I(III) compound

Scheme 31. Cyclization/migration of enaminones to substituted pyrrolin-4-ones in the presence of PIFA

Scheme 32. Cyclization/migration of 2-allylanilines to indolin- 3-ylmethanols mediated by I(III) species prepared in situ from the interaction of PhI and mCPBA

Scheme 33. Cyclization/migration of 2-alkenylanilines to indoles analogues mediated by I(III) compound PISA

Scheme 34. Cyclization/migration of N-methyl-N-phenylcinna- mamides to 3-phenylquinolin-2-ones mediated by PIFA

Scheme 35. Cyclization/rearrangement of 1,3,5-trialkylbenzenes to access carbazoles with PIDA

Scheme 36. Cyclization/rearrangement of biarylsulfonanilides to carbazole derivatives with PIDA or in situ formed I(III) species

Scheme 37. Difluorinated 1,2-migration of substituted or unsubstituted styrenes with in situ generated ArIF2

Scheme 38. General mechanism of difluorination/migration of substituted or unsubstituted styrenes

Scheme 39. Difluorination/migration of styrenes mediated by λ3-iodane 189 and AgBF4

Scheme 40. Fluorinated migration of unsaturated carboxylic acids to lactones mediated by λ3-iodane 189

Scheme 41. Fluorinated migration of 2-alkenylanilines to 4-fluoro-1,3-benzoxazepines triggered by λ3-iodane 189

Scheme 42. Fluorination/migration cascade of phenylallenes to α-difluoromethyl styrenes mediated by TolIF2

Scheme 43. Effective transformation of alkenyl MIDA boronates to prepare α-and β-difluorinated alkylborons mediated by in situ formed ArIF2

Scheme 44. One-pot two-step procedure of alkynes to α- or β-difluorinated alkyl azides mediated by in situ formed PhIF2

Scheme 45. Difluorination/1,2-halo-migration of α- or β-bromostyrenes by employing in situ formed PhIF2

Scheme 46. Asymmetric difluorination/migration of alkenes to difluoro methylated stereocenters mediated by in situ chiral formed ArIF2

Scheme 47. Asymmetric difluorination/bromo-migration of α-bromostyrenes to β,β-difluoroalkyl bromide compounds mediated by in situ chiral formed ArIF2

Scheme 48. Difluorination/migration of alkenes mediated by in situ formed p-TolIF2

Scheme 49. Stoichiometric and catalytic fluorination/migration of arylalkenes to difluorinated aromatic olefins via in situ generated ArIF2

Scheme 50. Stoichiometric and catalytic fluorination/migration of arylalkenes to difluorinated aromatic terminal olefins via in situ generated ArIF2

Scheme 51. Radical trifluoromethylation/1,2-shift of allylic alcohols by employing Togni’s reagent and copper catalyst

Scheme 52. Radical trifluoromethylation/1,2-shift of allylic alcohols to β-trifluoromethyl ketones analogues by employing Togni’s reagent and Fe(II) calalyst

Scheme 53. Radical trifluoromethylation/migration of homopropargylic alcohols to trifluoromethylated 3-butenals by utilizing Togni’s reagent and CuI catalyst

Scheme 54. Ring contraction of steroids via Favorskii rearrangement mediated by hypervalent iodine compounds.

Scheme 55. Ring contraction of steroids mediated by hypervalent iodine compounds

Scheme 56. Ring contraction of 1,4-naphthoquinones and diones via Wolff-type rearrangement triggered by PIDA

Scheme 57. Ring contraction of 1,4-naphthoquinones via Wolff-type rearrangement mediated by PIDA

Scheme 58. Ring contraction of flavanones in the presence of PIDA or HTIB and TMOF

Scheme 59. Ring contraction of flavanones and 1-benzosuberone in the presence of HMBI and TMOF

Scheme 60. Ring contraction of cycloalkanones in the presence of PIDA

Scheme 61. Ring contraction of cycloolefines mediated by λ3-iodane species 297, 298 or 299

Scheme 62. Hypervalent iodine mediated ring contraction of cycloolefines under different conditions

Scheme 63. Ring contraction of glycals triggered by HTIB

Scheme 64. Difluorination/ring contraction of cyclohexenes by employing p-TolIF2 and Et3N-5HF

Scheme 65. Difluorination/ring contraction of 1,2-dihydronaph- thalene mediated by λ3-iodane 189 and Pd(MeCN)4(BF4)2 or Cu(MeCN)4PF6

Scheme 66. Monofluorination/ring contraction of cyclohexenes mediated by in situ formed I(III) species 319

Scheme 67. Asymmetric ring contraction of cyclohexenes by utilizing HTIB in MeOH or CH3CN

Scheme 68. Asymmetric ring contraction of cyclohexenes mediated by in situ formed chiral I(III) compound 332

Scheme 69. Ring contraction of 3-hydroxypiperidine to lactams in the presence of PhIO and H2O

Scheme 70. Ring contractive cyanation of exocyclic β-enaminones to prepare cyanocyclopentanone derivatives in the presence of HTIB and NaN3

Scheme 71. Ring contraction of cyclobutanols to access aryl cyclopropyl ketones mediated by in situ formed PhI(OTf)2

Scheme 72. Fluorination/semipinacol rearrangement cascade of 2-alkylidenecyclobutanol analogues triggered by in situ formed PhIF2?HF

Scheme 73. Ring expansion of trimethylsilyloxycyclopropanols and oxysilane in the presence of PhIO and tetrabutylammonium fluoride

Scheme 74. Oxidative ring expansion of spirocycles mediated by HTIB

Scheme 75. Oxidative ring expansion of 1,5-diazadecalin to access bislactam triggered by (PhIO)n or (PhIO)n in situ generated from PIDA under base

Scheme 76. Ring expansion of cyclopentyl bromoalkynols and cyclopentyl iodoalkynol involving HTIB

Scheme 77. Ring expansion of cycloalkynols involving hypervalent iodine reagent

Scheme 78. Ring expansion of silyl or methyl ether mediated by HTIB

Scheme 79. Azidation/ring expansion of silylated cyclobutanols to prepare azidated cyclopentanones triggered by ABZ

Scheme 80. I(III) compounds-mediated ring expansion of alcohols

Scheme 81. Domino reaction of 1-(p-hydroxyaryl)cyclobutanols to prepare spiro cyclohexadienone lactones mediated by PIDA

Scheme 82. I(III) species-mediated oxidative ring expansion of cyclic ethers

Scheme 83. HTIB-mediated oxidative ring expansion of exocyclic alkenes to β-benzocycloalkenones.

Scheme 84. I(III) species-mediated oxidative ring expansion of exocyclic alkenes to ketone

Scheme 85. Domino λ3-iodanation/1,4-halogen shift/ring enlargement/fluorination of alkynes mediated by p-TolIF2

Scheme 86. Difluorination/ring expansion of exocyclic alkenes induced by λ3-iodane 189 and Pd(MeCN)4(BF4)2 or Cu(MeCN)4PF6

Scheme 87. p-TolIF2-mediated difluorinative ring expansion of heterocycles and allene-containing substrates

Scheme 88. One-pot PIDA-triggered oxidative reaction of of 2-arylindoles leading to 2-arylbenzoxazinones

Scheme 89. PIDA-triggered Wagner-Meerwein rearrangement or Prins-pinacol tandem of tertiary alcohols containing a phenolic moiety

Scheme 90. General procedure of I(III)-mediated Hoffman rearrangement of amides

Scheme 91. Hoffman rearrangement of amides mediated by common and unusual λ3-iodanes

Scheme 92. Hoffman rearrangement of amides to terminal amides with I(III) compounds 464

Scheme 93. Hoffman rearrangement of β-substituted amides with PIDA under basic conditions

Scheme 94. PSDIB-mediated Hoffman rearrangement of amino acid

Scheme 95. PIFA-mediated Hoffman rearrangement of 2-hydroxymethylbenzamides

Scheme 96. PIDA-mediated Hoffman rearrangement of asparagines and glutamines

Scheme 97. A Hoffman rearrangement/cyclization tandem of amides to isoquinolines and indoles

Scheme 98. Synthesis of quinolones from 2-alkynylbenzamides involving a PIDA-triggered Hoffman rearrangemen

Scheme 99. Synthesis of one-carbon dehomologated nitriles from primary carboxamides involving a IBX/TEAB-triggered Hoffman rearrangement

Scheme 100. Synthesis of one-carbon-shorter ketones from α,α-disubstituted acetamides involving a IBX-triggered Hoffman rearrangement.

Scheme 101. I(III)-Mediated Curtius rearrangement of azides leading to carbamoyl azides

Scheme 102. PhICl2-Mediated Curtius rearrangement of alcohols

Scheme 103. Beckmann rearrangement mediated by λ3-iodane

Scheme 104. C-N migration N-substituted amidines mediated by PIDA

Scheme 105. C-N migration of N-H ketimines by employing PIFA

Scheme 106. C-N migration of primary and secondary amines triggered by PIDA

Scheme 107. C-N migration of imidazo[1,2-a]pyridines to prepare imidazo[1,2-a]pyridin-3-amines by employing by PIDA

Scheme 108. One-pot PIFA-induced ring expansion/lactami- zation of cyclopentanones to N-aryl-δ-valerolactams

Scheme 109. PhI(OPiv)2-mediated C-N migration/cyclization of N-benzyl-2-aminopyridines

Scheme 110. PIDA-mediated oxidative rearrangement of 3-hydroxybut-2-enimidates

Scheme 111. Oxidative rearrangement of α-oxo-ketene N,N-acetals mediated by PIDA

Scheme 112. Ring expansion/fluorination of cyclopropanes to fluoropiperidines triggered by I(III) reagent 554

Scheme 113. 1,4-Radical migration of γ,γ-disubstituted triflic amides mediated by PIFA and sliver catalyst

Scheme 114. Exclusive intramolecular oxidative migration/ cyclization of N-phenylbenzamides and amides triggered by PIDA

Scheme 115. Oxidative rearrangement of alcohols mediated by bis(pyridinium) hypervalent iodine reagent

Scheme 116. PIDA-mediated oxidative ring expansion of bicyclo[4.2.0]octanols to access dihydrofuran-containing polycyclic aromatics

Scheme 117. N-C migration of imides to α,α-dialkylated α- hydroxy carboxylamides triggered by bromo-containing λ3-iodane 575 formed in situ

Scheme 118. Stevens rearrangement of ethers to 2-substituted- 3-p-toluenesulfonyldihydrofurans involving λ3-iodane compound

Scheme 119. Radical trifluoromethylation/migration/desulfonylation cascade of tosyl amides mediated by the combination of Togni’s reagent and CuI calalyst

Scheme 120. Radical azidation/aryl migration/desulfonylation cascade of ascade of tosyl amides mediated mediated by λ3-iodane 608

Scheme 121. PIDA-mediated aryl ipso-rearrangement of phenolic derivatives to ketones.

Scheme 122. Hypervalent iodine-mediated I-C migratory transformations

Scheme 123. Smiles rearrangement of allyl alcohol to access ether mediated by λ3-iodane species

Scheme 124. Smiles rearrangement of aryliodonio-quinoline- 8-olates involving λ3-iodane species

Scheme 125. Intramolecular aryl-migration of diaryliodonium salts

Scheme 126. Diarylation of N- and O-nucleophiles in the presence of diaryliodonium salt 634 via aryl rearrangement

Scheme 127. Earliest examples of the iodonio-Claisen manifold

Scheme 128. Recent developments of [3,3]-sigmatropic rearrangement of substituted λ3-iodanes with substituted allyl(trimethyl)silianes

Scheme 129. Nucleophiles proved to be suitable for reductive “iodonio-Claisen” rearrangement (RICR)

Scheme 130. Double functionalization of C—I(III) and/or ortho C—H bonds with diaryliodonium salts

Scheme 131. O-arylation/[3,3]-rearrangement tandem of oximes to benzo[b]furans

Scheme 132. Access to benzo[b]furans via the one-pot two-step O-arylation/[3,3]-shift of oximes with diaryliodonium salts

Scheme 133. Access to benzofuroindoline and pyrroloindoline via the O-arylation/[3,3]-shift/cyclization cascade of N-hydroxyindole with diaryliodonium salts

Scheme 134. Access to benzoxazoles via the two-step base-free O-arylation/[3,3]-shift/cyclization of amidoximes with diaryliodonium salts

Scheme 135. Access to indolines via a one-pot two-step N-arylation/[3＋2] cycloaddition/[3,3]-shift of alkynyl tethered oximes and diaryliodonium salts

Scheme 136. O-arylation/[3,3]-shift tandem of 667 and 668 involving diaryliodonium salts

Scheme 137. [3,3]-Sigmatropic rearrangement involving diaryliodonium salts

Scheme 138. Access to NOBIN or BINAMs via the one-pot two-step arylation/[3,3]-shift of (naphthalen-2-yloxy)carbamates or N-arylhydrazines with diaryliodonium salts

Scheme 139. Multiple [3,3]-rearrangement of N-phenoxyamides in the presence of alkynylbenziodoxolones

Scheme 140. Tandem reactions involving [3,3]-rearrangement of arylhydroxylamines with alkenyl-containing λ3-iodanes

Scheme 141. Access to enones via I(III)-oxidized [3,3]-rearrangement of tertiary allylic alcohol

Scheme 142. Oxidative fluoroarylation of benzylidenecyclopropanes with aryl iodides and HF?Py triggered by in situ formed aryl I(III) spices 726 via [3,3]-rearrangement

Scheme 143. PhIO-mediated [2,3]-sigmatropic rearrangement of allylic hydrazides to amines

Scheme 144. Arylation/1,3-radical rearrangement cascade involving diaryliodonium salts

Scheme 145. para-Selective C—H (α-borylbenzylation) of benzylic compounds and λ3-iodane 742 via a plausible [5,5]- sigmatropic rearrangement

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