Recent Progress on 1,2-Metallate Shift Reactions Based on Tetracoordinate Boron Intermediates

doi:10.6023/cjoc202110017

Abstract

Organoboron compounds are important and versatile synthetic building blocks in synthetic chemistry. Owing to the unique characteristics, they manifest great value in organic synthesis. In view of the versatile transformations, migration reactions of organoboron compounds have attracted great attention from chemists in recent years due to their high efficiency and mild reaction conditions, which are widely utilized for rapid constructions of carbon-carbon and carbon-heteroatom bonds. Recent progress on 1,2-migration reactions based on tetracoordinate boron intermediates is summarized according to various reaction conditions and bond formations.

Key words: carbon-carbon and carbon-heteroatom bonds, tetracoordinate boron intermediates, 1,2-migration reactions

Cite this article

Feng Zhang, Lu Zhou, Kai Yang, Qiuling Song. Recent Progress on 1,2-Metallate Shift Reactions Based on Tetracoordinate Boron Intermediates[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1013-1032.

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Fig. & Tab. 76

Scheme 1. Migration reactions based on tetracoordinate boron complexes

Scheme 2. Halogen-induced 1,2-migration of tetracoordinate boronate complex

Scheme 3. Synthesis of allylic gem-silylboryl alkanes

Scheme 4. Synthesis of boryl (germyl) (silyl) (stannyl) methane

Scheme 5. Synthesis of 3-boryl-3-silylcyclobutene

Scheme 6. Stereodivergent synthesis of tertiary alcohols

Scheme 7. Asymmetric synthesis of allylsilanes

Scheme 8. Stereospecific mono- and difluoromethylation of boronic esters

Scheme 9. Synthesis of α-boryl aldehydes

Scheme 10. Deoxygenative gem-diborylation and gem-silyl- borylation of aldehydes and ketones

Scheme 11. gem-Carboborylation of aldehydes and ketones

Scheme 12. Transition-metal-free C(sp3)—C(sp2) cross-coupling reaction

Scheme 13. Synthesis of 1,1-disubstituted vinyl boronic esters

Scheme 14. Synthesis of tertiary α-trifluoromethylated boronic esters

Scheme 15. Modular synthesis of azetidines

Scheme 16. Difunctionalization of bicyclo[1.1.0]butyl boronate complexes

Scheme 17. 1,2-Metallate rearrangement induced by ring expansion of vinyl cyclopropyl boronate complexes

Scheme 18. Deoxygenative arylation of aromatic amides with arylboronic esters

Scheme 19. Enantioselective catalytic 1,2-boronate rearrangement

Scheme 20. 1,2-Migration between trialkylboranes and carbon monoxide

Scheme 21. Stereoselective synthesis of alkenes via Zweifel olefination ractions

Scheme 22. Proton-induced 1,2-migration of lithium Ethynyltrialkylborates

Scheme 23. 1,2-Migration of etheny- and ethynylsilylboranes

Scheme 24. Synthesis of 1,1-diborylalkenes or 1-boryl-1-silylalkenes

Scheme 25. Enantiospecific sp2-sp3 coupling of alkyl boronic esters

Scheme 26. Brønsted base-catalyzed reaction between terminal alkynes and bis(pinacolato)diboron

Scheme 27. Stereodivergent olefination of enantioenriched boronic esters

Scheme 28. Synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane

Scheme 29. Boryl-anion migration induced by soft borane Lewis acid

Scheme 30. Enantioselective, lewis base-catalyzed carbosulfenylation of alkenylboronates

Scheme 31. Electrophilic fluoroalkylthiolation induced diastereoselective 1,2-metallate migration of alkenylboronates

Scheme 32. Boronic ester-induced consecutive double 1,2- migration reactions

Scheme 33. Stereoselective base-catalyzed 1,1-silaboration of terminal alkynes

Scheme 34. Quadruple borylation of terminal alkynes

Scheme 35. Transition-metal-free double-insertive coupling for diarylmethanamine synthesis

Scheme 36. Reductive coupling reaction between boronic acids and tosylhydrazones

Scheme 37. Olefination of carbonyl compounds between acids and tosylhydrazones

Scheme 38. Domino carbocyclizations n?tosylhydrazones with alkenylboronic acids

Scheme 39. Synthesis of pinacol alkylboronates from tosylhydrazone

Scheme 40. gem-Diborylation and gem-silylborylation of N- tosylhydrazones

Scheme 41. Synthesis of α-aryl esters and nitriles from arylboronic acids

Scheme 42. Synthesis α-trifluoromethylated alkylboron compounds

Scheme 43. Synthesis of unsymmetrical 1,1-diborated compounds

Scheme 44. Trimethylsilyldiazomethane insertion into pinB-SR

Scheme 45. C(sp2)—C(sp2) cross coupling of diazo quinones with catechol boronic esters

Scheme 46. Oxidation of arylboronic acids with hydrogen peroxide

Scheme 47. Oxidation of arylboronic acids with hydroxylamine

Scheme 48. Hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides

Scheme 49. Reaction of acyltrifluoroborate with azides

Scheme 50. Amination of arylboronic acids with electrophilic aminating agents

Scheme 51. Direct stereospecific amination of alkyl and aryl pinacol boronates

Scheme 52. Electrophilic amination of arylboroxine with O-benzoyl hydroxylamin

Scheme 53. Synthesis of primary anilines with H2N-OSO3H

Scheme 54. Synthesis of di(hetero)arylamines from nitrosoarenes and boronic acids

Scheme 55. Amination of organoboronic acids with N-alkyl hydroxylamines

Scheme 56. Amination for alkyl and aryl pinacol boronates with H2N-DABCO

Scheme 57. 1,2-Migration of alkynyl boronate complex induced by iron salt

Scheme 58. Pd(allyl) complex-catalyzed synthesis of 1,4-dienes

Scheme 59. Pd-catalyzed coupling of alkynyl boronate complexes and aryl bromides

Scheme 60. Pd-catalyzed coupling of alkynyl-9-BBN ‘ate’ complexes with aryl bromides

Scheme 61. Silver-catalyzed hydroalkylation of alkynes

Scheme 62. Pd-catalyzed addition of indole boronates complexes to allyl electrophiles

Scheme 63. Transition-metal-catalyzed asymmetric coupling of indolylboronate complexes and allyl acetates

Scheme 64. Pd-catalyzed enantioselective conjunctive cross-coupling of alkenylboronate complexes

Scheme 65. Ni-catalyzed enantioselective conjunctive cross- coupling of alkenylboronate complexes

Scheme 66. Ni-catalyzed conjunctive coupling of alkenylboronate complexes with C(sp3) electrophiles

Scheme 67. Lewid acid-catalyzed asymmetric 1,2-migration

Scheme 68. Pd-catalyzed ring-opening 1,2-migration reaction of strained bicycles

Scheme 69. Design for radical-polar crossover reaction of vinyl boronate complexes

Scheme 70. Stereospecific radical-polar crossover reaction of chiral boronic esters

Scheme 71. Radical-polar crossover reaction of dienyl boronate complexes

Scheme 72. Radical-induced 1,2-migration of vinyl boronate complexes

Scheme 73. Radical-induced 1,2-migration of heteroarenes with boronic esters

Scheme 74. Synthesis of cyclobutyl boronic esters via radical- induced strain-increase ring contraction

Scheme 75. Radical-induced 1,2-migration of bicyclobutane boronate complexes

Scheme 76. HAT induced coupling of alkyl boronic esters with organometallic reagents

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基于四配位硼的1,2-迁移反应研究进展