基于四配位硼的1,2-迁移反应研究进展

doi:10.6023/cjoc202110017

摘要/Abstract

有机硼化合物是合成方法学中重要且通用的合成骨架. 由于其独特的性质, 它们在有机合成中表现出巨大的价值. 有机硼化合物具有丰富的转化能力, 近年来, 由于其迁移反应高效、反应条件温和而受到了化学家们的广泛关注, 用于快速构建各种碳碳键和碳杂键. 本篇综述根据不同的反应条件和键的形成, 系统总结了近年来基于四配位硼中间体的1,2-迁移反应.

关键词: 碳碳键和碳杂键, 四配位硼中间体, 1,2-迁移反应

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

引用此文

张锋, 周鹿, 杨凯, 宋秋玲. 基于四配位硼的1,2-迁移反应研究进展[J]. 有机化学, 2022, 42(4): 1013-1032.

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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图/表 76

图式1. 基于四配位硼的迁移反应

Scheme 1. Migration reactions based on tetracoordinate boron complexes

图式2. 卤素诱导的的四配位硼酸酯络合物的1,2-迁移

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

图式3. 烯丙基偕硅硼烷的合成

Scheme 3. Synthesis of allylic gem-silylboryl alkanes

图式4. 硼、铬、硅、锡取代甲烷的合成

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

图式5. 3-硼烷-3-硅烷环丁烯骨架的合成

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

图式6. 立体多样性的三级醇的合成

Scheme 6. Stereodivergent synthesis of tertiary alcohols

图式7. 对映选择性烯丙基硅烷的合成

Scheme 7. Asymmetric synthesis of allylsilanes

图式8. 硼酸酯的立体选择性的单氟和二氟甲基化

Scheme 8. Stereospecific mono- and difluoromethylation of boronic esters

图式9. α-硼取代醛的合成

Scheme 9. Synthesis of α-boryl aldehydes

图式10. 醛或酮的脱氧偕二硼化或偕硅硼化反应

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

图式11. 醛或酮的偕碳硼化反应

Scheme 11. gem-Carboborylation of aldehydes and ketones

图式12. 无过渡金属条件下的C(sp3)—C(sp2)偶联反应

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

图式13. 1,1-二取代烯基硼酸酯的合成

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

图式14. α-三氟甲基三级硼酸酯的合成

Scheme 14. Synthesis of tertiary α-trifluoromethylated boronic esters

图式15. 氮杂环丁烷的模块化合成

Scheme 15. Modular synthesis of azetidines

图式16. 双环[1.1.0]丁基硼酸酯络合物的双官能团化反应

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

图式17. 环丙基乙烯基硼酸酯络合物的扩环诱导的1,2-迁移反应

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

图式18. 芳香酰胺和芳基硼酸的脱氧芳基化反应

Scheme 18. Deoxygenative arylation of aromatic amides with arylboronic esters

图式19. 对映选择性催化的硼酸酯的1,2-迁移反应

Scheme 19. Enantioselective catalytic 1,2-boronate rearrangement

图式20. 1-2三烷基硼的和一氧化碳的1,2-迁移反应

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

图式21. Zweifel烯基化反应立体选择性合成烯烃

Scheme 21. Stereoselective synthesis of alkenes via Zweifel olefination ractions

图式22. 质子诱导的炔基硼酸酯的1,2-迁移

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

图式23. 烯基或炔基硅硼烷的1,2-迁移

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

图式24. 1,1-烯基偕二硼和偕硅硼烷的合成

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

图式25. 烷基硼酸酯对映选择性的sp2-sp3的偶联反应

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

图式26. 布朗斯特碱催化的末端炔烃和联硼酸频哪醇酯的反应

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

图式27. 富含手性的硼酸酯立体多样性的烯基化反应

Scheme 27. Stereodivergent olefination of enantioenriched boronic esters

图式28. 1,3-二取代双环[1.1.1]戊烷的合成

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

图式29. 软硼路易斯酸诱导的硼负离子的迁移

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

图式30. 对映选择性路易斯碱催化的烯基硼酸酯的碳硫化反应

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

图式31. 亲电氟烷基硫试剂诱导的烯基硼酸酯的1, 2-迁移反应

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

图式32. 硼酸酯诱导的连续的双1,2-迁移反应

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

图式33. 立体选择性碱催化的1,1-烯基偕硅硼烷的合成

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

图式34. 末端炔烃的四硼化反应

Scheme 34. Quadruple borylation of terminal alkynes

Scheme 35. 无过渡条件下的双插入偶联合成二芳基甲胺

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

图式36. 硼酸和腙的还原偶联反应

Scheme 36. Reductive coupling reaction between boronic acids and tosylhydrazones

图式37. 烯基硼酸与腙的烯基化反应

Scheme 37. Olefination of carbonyl compounds between acids and tosylhydrazones

图式38. 腙和烯基硼酸的多米诺环化反应

Scheme 38. Domino carbocyclizations n?tosylhydrazones with alkenylboronic acids

图式39. 从腙出发合成烷基硼酸酯类化合物

Scheme 39. Synthesis of pinacol alkylboronates from tosylhydrazone

图式40. 无过渡金属条件下腙合成烷基偕二硼和偕硅硼化合物

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

图式41. 由硼酸出发合成α-芳基酯和α-芳基腈类化合物

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

图式42. α-三氟甲基烷基硼化合物的合成

Scheme 42. Synthesis α-trifluoromethylated alkylboron compounds

图式43. 不对称1,1-二硼类化合物的合成

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

图式44. 三甲基硅基重氮甲烷对硫硼烷的插入反应

Scheme 44. Trimethylsilyldiazomethane insertion into pinB-SR

图式45. 重氮喹啉酮与儿茶酚硼酸酯的C(sp2)—C(sp2)偶联反应

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

图式46. 过氧化氢氧化芳基硼酸

Scheme 46. Oxidation of arylboronic acids with hydrogen peroxide

图式47. 羟胺氧化芳基硼酸

Scheme 47. Oxidation of arylboronic acids with hydroxylamine

图式48. 芳基或杂环芳基硼酸或硼酸酯与氮氧化合物的羟基化反应

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

图式49. 酰基三氟硼酸钾与叠氮化和物的反应

Scheme 49. Reaction of acyltrifluoroborate with azides

图式50. 亲电胺化试剂实现芳香硼酸的胺化反应

Scheme 50. Amination of arylboronic acids with electrophilic aminating agents

图式51. 芳基或烷基硼酸酯的直接立体选择性的胺化反应

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

图式52. O-苯甲酰羟胺参与的硼酸酐的亲电胺化反应

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

图式53. 氨基磺酸促进的一级胺的合成

Scheme 53. Synthesis of primary anilines with H2N-OSO3H

图式54. 亚硝基苯与硼酸合成二芳基胺

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

图式55. N-烷基羟胺参与的有机硼酸的胺化反应

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

图式56. H2N-DABCO参与的烷基或芳基硼酸酯的胺化反应

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

图式57. 铁盐诱导的炔基硼酸酯络合物的1,2-迁移

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

图式58. 烯丙基钯催化的1,4-丁二烯的合成

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

图式59. 钯催化的炔基硼酸酯络合物与芳基溴代物的偶联

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

图式60. 钯催化炔基9-BBN酯络合物与芳基溴化物的偶联反应

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

图式61. 银催化的炔烃的氢芳基化反应

Scheme 61. Silver-catalyzed hydroalkylation of alkynes

图式62. 钯诱导的吲哚硼络合物对烯丙基亲电试剂的加成反应

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

图式63. 过渡金属催化吲哚硼酸酯络合物与烯丙基酯不对称偶联反应

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

图式64. 钯催化的烯基硼酸酯络合物对映选择性连接交叉偶联

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

图式65. 镍催化的烯基硼酸酯络合物对映选择性连接交叉偶联

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

图式66. 镍催化烯基硼酸酯络合物与C(sp3)亲电试剂的连接交叉偶联

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

图式67. 路易斯酸催化的不对称1,2-迁移

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

图式68. 钯催化的张力双环开环的1,2-迁移反应

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

图式69. 乙烯基硼酸酯络合物自由基极性交叉反应的设计

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

图式70. 立体选择性的手性硼酸酯的自由基极性交叉反应

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

图式71. 二烯基硼酸盐配合物的自由基极性交叉反应

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

图式72. 自由基诱导的乙烯基硼酸盐的1,2-迁移反应

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

图式73. 自由基诱导的杂环和硼酸酯的1,2-迁移反应

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

图式74. 光诱导的增环张力的缩环反应合成环丁基硼酸酯

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

图式75. 自由基诱导的双环丁烷硼酸酯的1,2-迁移

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

图式76. 氢原子转移诱导的烷基硼酸酯与有机金属试剂的偶联

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

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