Advances in Asymmetric Electrochemical Synthesis

doi:10.6023/cjoc202402005

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 673-727.DOI: 10.6023/cjoc202402005 Previous Articles Next Articles

Special Issue: 光电催化综述合集

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电化学不对称合成反应的研究进展

高淳, 刘欣, 王明慧, 刘淑贤, 朱婷婷, 张怡康, 郝二军^*(), 杨启亮^*()

河南师范大学化学化工学院抗病毒性传染病创新药物全国重点实验室平原实验室绿色化学介质与反应教育部重点实验室精细化学品绿色制造河南省协同创新中心河南新乡 453007

收稿日期:2024-02-03 修回日期:2024-03-02 发布日期:2024-04-02
基金资助:
国家自然科学基金(22007028); 河南省自然科学基金(232300421126); 河南师范大学科研启动经费(5101039170920); 大学生创新创业训练计划(202310476058); 大学生创新创业训练计划(202310476055)

Advances in Asymmetric Electrochemical Synthesis

Chun Gao, Xin Liu, Minghui Wang, Shuxian Liu, Tingting Zhu, Yikang Zhang, Erjun Hao(), Qiliang Yang()

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2024-02-03 Revised:2024-03-02 Published:2024-04-02
Contact: *E-mail: yangqiliang@htu.edu.cn; hej@htu.edu.cn
Supported by:
National Natural Science Foundation of China(22007028); Natural Science Foundation of Henan Province(232300421126); Henan Normal University Initiation Fund(5101039170920); College Students Innovative Entrepreneurial Training Plan Program(202310476058); College Students Innovative Entrepreneurial Training Plan Program(202310476055)

Asymmetric synthesis is one of the most important and valuable frontiers in exploratory research of synthetic organic chemistry. With the renaissance and vigorous development of organic electrochemistry in recent years, combining electrochemical organic synthesis and asymmetric catalytic strategies can be used to expand the reaction types, activation modes, bond formation systems, and substrate adaptability of asymmetric catalysis using the benefits of organic electrochemistry, which brought new opportunities for the asymmetric transformation that is difficult or impossible to be achieved by traditional methods. Thus, the development of novel, efficient, precise and sustainable electrochemical asymmetric catalytic strategies under mild and eco-friendly conditions is of great research significance. Although there are many advantages and key advances in asymmetric electrocatalysis, major challenges remain. Until now, relatively few examples of asymmetric electrochemical transformations with high enantioselectivity have been reported. In recent years, scholars in the field of organic chemistry around the world have carried out a series of original works in the field of asymmetric electro- chemical catalysis, and achieved remarkable results. The theoretical innovation, technical breakthrough, and difficult challenges in asymmetric electrochemical synthesis in recent decades are summarized. Examples of enantioselective electro-organic synthesis using transition metal catalysts, organocatalysts, biological enzyme catalysts, chemically modified chiral electrodes, chiral electrolytes, chiral solvents and chiral auxiliaries are discussed, along with their related reaction machanistic aspects. Finally, perspectives on this cutting-edge area are also briefly discussed.

Key words: organic electrosynthesis, asymmetric catalysis, enantioselectivity, transition-metal catalysis, organocatalysis

Cite this article

Chun Gao, Xin Liu, Minghui Wang, Shuxian Liu, Tingting Zhu, Yikang Zhang, Erjun Hao, Qiliang Yang. Advances in Asymmetric Electrochemical Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 673-727.

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Fig. & Tab. 97

Scheme 1. General classification of asymmetric organic electrosynthesis

Scheme 2. Cell notations (left), and electrochemical asymmetric reaction activation mode (right)

Scheme 3. OsO4-catalyzed asymmetric electrochemical dihydroxylation of olefins

Scheme 4. K2OsO2(OH)4 catalyzed asymmetric electrochemical dihydroxylation of olefins

Scheme 5. Electrochemical asymmetric dihydroxylation reaction for the synthesis of chiral acyclic nucleosides

Scheme 6. Asymmetric electrochemical epoxidation of olefins catalyzed by Mn-salen complexes

Scheme 7. Asymmetric electrochemical transformation mediated by hydrophobic vitamin B12

Scheme 8. Chiral Co-salen complex catalyzed electrochemical asymmetric carboxylation of benzyl chloride

Scheme 9. Electrooxidative Co-catalyzed regio- and enantioselective annulation of benzamides with alkenes

Scheme 10. Co/Salox-catalyzed electrochemical enantioselective C—H alkoxylation

Scheme 11. Electro-oxidative cobalt-catalyzed enantioselective C—H and N—H annulations to access C-stereogenic molecules

Scheme 12. Electro-oxidative cobalt-catalyzed enantioselective C—H/N—H annulations to access P-stereogenic molecules

Scheme 13. Co-catalyzed electrochemical asymmetric [4＋2] annulation of arylphosphinic amides and alkynes

Scheme 14. Electrooxidative Co-catalyzed enantioselective annulation of alkenes

Scheme 15. Co/Salox-catalyzed electrochemical asymmetric C—H/N—H annulation of aryl sulfonamides with alkynes

Scheme 16. Electrochemical Co-catalyzed atroposelective C—H activation/annulation to access N—N axially chiral frameworks

Scheme 17. Electrochemical Co-catalyzed synthesis of C—N axially chiral pyridine-N-oxides

Scheme 18. Electro-reductive Co-catalyzed enantioselective intramolecular cyclization of 1,6-enyne

Scheme 19. Ni-catalyzed asymmetric electrochemical reduction cleavage of allyl β-ketone esters

Scheme 20. Ni-catalyzed asymmetric electroreductive cross- coupling of alkenyl bromide and benzyl chloride

Scheme 21. Ni-catalyzed asymmetric electrochemical reductive homocoupling of aryl bromides

Scheme 22. Paired electrolysis-enabled nickel-catalyzed asymmetric reductive cross-coupling between α-chloroesters and aryl bromides

Scheme 23. Ni-catalyzed asymmetric electrochemical reductive cross-coupling of aryl aziridines with aryl iodides

Scheme 24. Ni-catalyzed asymmetric electrochemical reductive cross-coupling of aryl aziridines with alkenyl bromides

Scheme 25. Ni-catalyzed asymmetric electrochemical alkylation of acylimidazoles

Scheme 26. Ni-catalyzed asymmetric electrochemical arylation of 2-acylimidazole with p-methylphenol

Scheme 27. Ni-catalyzed asymmetric electrochemical radical allylation

Scheme 28. Ni-catalyzed switchable asymmetric electrochemical difunctionalization and alkenylation of alkenes

Scheme 29. Ni-catalyzed asymmetric electrochemical cross-dehydrogenative amination with acylimidazoles

Scheme 30. Ni-catalyzed electrochemical coupling of 2-acylimidazoles with thiophenols to construct asymmetric C—S bonds

Scheme 31. Asymmetric olefin-sulfonylimine cross-coupling via paired electrocatalysis

Scheme 32. Ni-catalyzed electrochemical asymmetric carboxylation reaction of acetophenone with CO2

Scheme 33. Parallel paired electrolysis for the simultaneous synthesis of aldehydes/aryl bromides and chiral alcohols

Scheme 34. Ni/Cu dual-catalyzed stereodivergent electrooxidative homocoupling of benzoxazolyl acetate

Scheme 35. Cu-catalyzed electrochemical asymmetric oxidation of 1,2-diols

Scheme 36. Cu-catalyzed asymmetric electrochemical difunctionalization of vinylarenes

Scheme 37. Co/Cu dual-catalyzed electrochemical asymmetric hydrocyanation of conjugated alkenes

Scheme 38. Cu-catalyzed cross-coupling of electrochemical asymmetric Shono-type oxidation

Scheme 39. Photoelectrocatalyzed site- and enantioselective cyanation of benzylic C—H bonds

Scheme 40. Ce/Cu-catalyzed electrophotochemical enantioselective decarboxylative cyanation

Scheme 41. Photoelectrocatalyzed asymmetric heteroarylcyanation of alkenes

Scheme 42. Pd-catalyzed asymmetric electrocarboxylation of allyl esters with carbon dioxide

Scheme 43. Pd-catalyzed electrochemical enantioselective synthesis of axially chiral biaryls

Scheme 44. Pd-catalyzed electrochemical asymmetric C—H olefinations and allylations

Scheme 45. Ru-catalyzed asymmetric electrochemical reduction of 2,2,2-trifluoroacetophenone

Scheme 46. Electro-oxidative Rh-catalyzed enantioselective C—H annulation with alkynes

Scheme 47. Electrochemical asymmetric cross-coupling reaction of 2-acylimidazole with enol silyl ether

Scheme 48. Rh-catalyzed electrochemical asymmetric α-C(sp3)—H alkenylation of 2-acylimidazole

Scheme 49. Photoelectrocatalyzed asymmetric dehydrogenative [2＋2] cycloaddition between alkyl ketones and alkenes

Scheme 50. Enantioselective electrochemical cathodic reduction of 4-methylcoumarin

Scheme 51. Asymmetric electrochemical reduction of ketoesters induced by β-cyclodextrin

Scheme 52. Asymmetric electrochemical carboxylation of acetophenone

Scheme 53. Quinine-catalyzed electrochemical enantioselective alkenylation of tetrahydroisoquinolines

Scheme 54. Enantioselective electrochemical oxidation of racemic sec-amines and alcohols using a chiral N-oxyl radical

Scheme 55. Electro-oxidative kinetic resolution of sec-alcohols using a chiral N-oxyl radical

Scheme 56. Electro-oxidative asymmetric α-oxyamination of aldehyde enabled by a chiral amine catalyst

Scheme 57. Electro-oxidative asymmetric α-alkylation of aldehyde enabled by a chiral amine catalyst

Scheme 58. Electro-oxidative asymmetric α-arylation of aldehyde enabled by a chiral amine catalyst

Scheme 59. Electro-oxidative asymmetric cross-coupling of tertiary amines with ketones catalyzed by a chiral amine catalyst

Scheme 60. Electro-oxidative asymmetric α-arylation of cyclic β-ketocarbonyls enabled by a chiral amine catalyst

Scheme 61. Electro-oxidative asymmetric coupling of acyclic amines with ketones catalyzed by L-proline

Scheme 62. Asymmetric electrosynthesis of C2-quaternary indolin-3-ones

Scheme 63. Squaramide-catalyzed electro-oxidative asymmetric detrifluoroacetylation

Scheme 64. Chiral imine ion salts catalyzed electrochemical asymmetric epoxidation of olefins

Scheme 65. Asymmetric electrochemical lactonization induced by chiral iodoarenes

Scheme 66. Atroposelective arene formation via electrochemical oxidative NHC organocatalysis

Scheme 67. Proposed mechanism of electrochemical oxidative NHC organocatalysis

Scheme 68. Iodide promoted electrochemical oxidative NHC organocatalysis system

Scheme 69. Electrochemical asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis

Scheme 70. Electroenzyme catalyzed asymmetric reduction of enoic acids

Scheme 71. Electroenzyme catalyzed asymmetric reduction of 3-methylcyclohexanone

Scheme 72. Electroenzyme catalyzed asymmetric epoxidation of styrene

Scheme 73. Electroenzyme catalyzed asymmetric oxidation of thioethers to sulfoxides

Scheme 74. Microbial electrosynthesis of chiral alcohols using escherichia coli

Scheme 75. Bioelectrocatalytic N2 fixation to access chiral amine intermediates

Scheme 76. Biphasic bioelectrocatalytic synthesis of chiral β-hydroxy nitriles

Scheme 77. Asymmetric electroreduction reactions induced by chemically modified chiral electrodes

Scheme 78. Asymmetric electrooxidation on chemically modified chiral electrodes

Scheme 79. Asymmetric electrochemical reactions induced by a TEMPO-modified chiral electrode

Scheme 80. Asymmetric hydrogenation induced by chiral bipyridine-Rh complexes modified chiral electrodes

Scheme 81. Asymmetric electroreduction of aromatic ketones induced by a chiral electrode

Scheme 82. Electrochemical asymmetric reduction of acetophenone induced by chiral supporting electrolyte

Scheme 83. Electrochemical asymmetric reduction of α-aminoketones induced by chiral supporting electrolyte

Scheme 84. Electrochemical asymmetric oxidation of enol acetates induced by chiral supporting electrolyte

Scheme 85. Electrochemical asymmetric reduction of acetophenone induced by chiral solvents

Scheme 86. Electrochemical asymmetric reduction of oxophenylacetamide induced by chiral auxiliaries

Scheme 87. Ni-catalyzed asymmetric electroreductive cross-coupling induced by chiral auxiliaries

Scheme 88. Mannich addition of silyloxyfuran to cyclic N-acyliminium ions containing cyclohexyl-based chiral auxiliaries

Scheme 89. Chiral auxiliary-induced electrochemical asymmetric reductive hydrocoupling of cinnamate esters

Scheme 90. Diastereoselective electrochemical carboxylation of chiral α-bromocarboxylic acid derivatives

Scheme 91. Electrochemical Michael addition of chiral acetoacetate derivatives to methyl vinyl ketone

Scheme 92. Stereoselective electrochemical carboxylation of cinnamic acid derivatives induced by chiral auxiliaries

Scheme 93. Electrochemical diastereoselective α-alkylation of pyrrolidines induced by chiral phosphorus auxiliaries

Scheme 94. Synthesis of chiral cis-β-lactams by chiral auxiliary-induced electrochemical cyclization of amides

Scheme 95. Diastereoselective anodic oxidation followed by intramolecular cyclization of chiral ω-hydroxyl amides

Scheme 96. Electrochemical deprotonation of Chiral Ni(II) glycinate: diastereoselective nucleophilic addition to Michael acceptors

Scheme 97. Electroreductive coupling of diaryl ketones with chiral α,β-unsaturated carbonyl compounds

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电化学不对称合成反应的研究进展

Advances in Asymmetric Electrochemical Synthesis

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