催化学报 ›› 2022, Vol. 43 ›› Issue (12): 3046-3061.DOI: 10.1016/S1872-2067(22)64180-9
Teera Chantarojsiri(), Tassaneewan Soisuwan, Pornwimon Kongkiatkrai
收稿日期:
2022-06-15
接受日期:
2022-09-28
出版日期:
2022-12-18
发布日期:
2022-10-18
通讯作者:
Teera Chantarojsiri
Teera Chantarojsiri(), Tassaneewan Soisuwan, Pornwimon Kongkiatkrai
Received:
2022-06-15
Accepted:
2022-09-28
Online:
2022-12-18
Published:
2022-10-18
Contact:
Teera Chantarojsiri
About author:
Teera Chantarojsiri earned her bachelor’s degree in chemistry from Stanford University in 2010 and received her Ph.D. in Chemistry from University of California, Berkeley in 2015. After a postdoctoral training at University of California, Irvine, she joined the Department of Chemistry, Faculty of Science, Mahidol University, Thailand in 2018 and she was promoted to an assistant professor in 2020. Currently, she is pursuing research in transition metal-mediated catalytic processes and electrocatalysis of small molecule activation.
摘要:
近年来, 人们一直在为缓解气候危机而努力, 电合成和CO2利用引起了研究者的广泛关注. 在过去十年中, CO2利用或有机物的电羧基化, 特别是有机卤化物及烯烃的电羧基化, 取得了较大进展. 电羧基化实验装置的各组成部分以及深入理解反应机理对羧酸盐的成功合成至关重要. 本文概述了电羧基化反应的机理和电化学反应装置, 阐明了各装置组成部分的重要性, 如不同阴极、牺牲阳极材料和其他添加剂的作用, 并以有机卤化物和烯烃的电羧基化反应为例进行了详细讨论. 最后, 讨论了该领域的发展趋势和未来研究方向.
Teera Chantarojsiri, Tassaneewan Soisuwan, Pornwimon Kongkiatkrai. 羧酸盐的绿色合成: 用于有机卤化物和烯烃电羧基化反应电极上的反应及其机理[J]. 催化学报, 2022, 43(12): 3046-3061.
Teera Chantarojsiri, Tassaneewan Soisuwan, Pornwimon Kongkiatkrai. Toward green syntheses of carboxylates: Considerations of mechanisms and reactions at the electrodes for electrocarboxylation of organohalides and alkenes[J]. Chinese Journal of Catalysis, 2022, 43(12): 3046-3061.
Scheme 1. Electrocarboxylation reaction mechanisms for different substrates. R represents alkyl or aryl groups. Proposed mechanisms for alkyl or aryl halides are shown in (a)?(d). Activation of alkenes are proposed and displayed in (e)?(h), while defluorinative carboxylation mechanisms of gem-difluoroalkene and α-CF3 alkenes are listed in (i)? (l).
Fig. 1. (a) Cyclic Voltammograms of o-dibromobenzne, m-dibromobenzene, p-dibromobenze, and bromobenzene with Ag electrode in 0.1 mol/L TBABF4 DMF, showed two successive reductive processes for m-dibromobenzne and p-dibromobenze, one 2-electron reduction for o-dibromobenzene, and one 1-electron reduction for bromobenzene. (b) Schematic representation of reductive debromination with m-dibromobenzene. (c) Cyclic Voltammograms of m-dibromobenzene with Ag electrode showed current enhancement upon exposure to CO2 atmosphere, compared to when CO2 was absent and background signal. (d) Cyclic voltammograms of m-dibromobenzene with different electrodes under N2. Reproduced with permission from Ref. [9], Copyright 2012, Elsevier. (e) Cyclic voltammograms of Ni-catalyzed aryl bromide electrocarboxylation. (f) Proposed catalytic cycle of carboxylation of arylbromide, catalyzed by Ni complex. Reproduced under the terms of the CC-BY 4.0 license from Ref. [15].
Scheme 2. Electrolyses experiments of 16 mmol/L 4-fluorobenzonitrile, in 0.1 mol/L TBABF4 DMF solution under N2, demonstrated the products from the protonation and the coupling of possible radical intermediates. Ag foil was used as a working electrode with Pt counter electrode and SCE reference electrode. Reprinted with permission from Ref. [12]. Copyright 2019, Elsevier
Fig. 2. Proposed reaction pathway for defluorinative carboxylation performed at the IEFPCM-M06-2X/6-311++G(d,p) level [14]. Reprinted with permission from Ref. [14]. Copyright 2020, the Royal Society of Chemistry.
Fig. 4. A chart representing a direct electrochemical process without redox mediators (left), and indirect electrochemical process with a redox mediator (right).
Fig. 5. Representative mechanism of phenyl bromide electrocarboxylation. Reductive debromination of bromobenzene yields phenyl radical that can be reduced again by the cathode to form phenyl radical anion, which can react with CO2 to form carboxylate product.
Fig. 6. Representative mechanism of benzyl bromide electrocarboxylation. Reduction of benzyl bromide generate a benzyl radical and a bromide ion. The radical proceeds to be one-electron reduced by the cathode, forming a radical anion which can react with CO2 to form the carboxylate product.
Fig. 7. Reductions of benzyl bromide from different electrode materials at 0.2 V/sin CH3CN with 0.1 mol/L TBAPF6 or TBABF4. Reproduced with permission from Ref. [33], Copyright 2005, Elsevier.
Fig. 8. Cathodic sweep of 100 mmol/L benzyl chloride, bromide, and iodide, showing the onset of reduction of each substrate by different metal cathodes. The voltammograms were recorded at 50 mV/s, under Ar atmosphere, in 0.1 TBABF4 MeCN solution. Reproduced with permission from Ref. [34], Copyright 2021, Elsevier.
Fig. 9. Cyclic voltammogram of 4-fluorobenzonitrile in 0.1 mol/L TBABF4 DMF solution at the scan rate 500 mV/s under CO2 atmosphere. (GC: glassy carbon electrode, Ag: silver electrode), Reproduced with permission from Ref. [12], Copyright 2019, Elsevier.
Fig. 10. Proposed mechanism and reactions at electrodes for electrocarboxylation of conjugated diene. Reproduced with permission from Ref. [22]. Copyright 2020, the Royal Society of Chemistry.
Fig. 11. Proposed mechanism for deflurinative carboxylation, showing reactions at each electrode. Adapted with permission from Ref. [14]. Copyright 2020, the Royal Society of Chemistry.
Fig. 12. Proposed reaction mechanism of aryl halides (a) and allylic halides (b). M, in both cases, represents Ni, Pd, Cu, and Co. Active catalysts, generally reduced species, undergo oxidative addition with aryl halides or allylic halides (step I), before being reduced by the electrode (step II). CO2 addition occurs in step III and products are released to regain active catalysts (step IV). Ligands that were used to support metal catalysts for electrochemical carboxylation (c).
Fig. 13. DFT calculations at the PW6B95-D4/def2-TZVPP+SMD(DMF) //TPSS-D3(BJ)/def2-SVP level of theory suggested the allylic C-C bond formation as the rate determining step, due to the higher reaction barrier. Reproduced with permission from Ref. [20], Copyright 2020, Wiley.
Fig. 14. Reactions at the electrode for three-component coupling of DMF, CO2, and benzyl halides using quasi-divided cell. Reproduced with permission from Ref. [39]. Copyright 2015, Elsevier.
Scheme 5. (a) Stabilization of carboxylate intermediates by Mg2+, Zn2+ and Al3+. (b) The plausible formation of Grignard type reagent. (c) The reduction of CO2 by Sm(II) and the stabilization of intermediate by Sm complex.
Fig. 15. Proposed reaction mechanism and reactions at each electrode for carboxylation of benzyl ammonium salts. Reproduced with permission from Ref [19]. Copyright 2019, the American Chemical Society
Substrate | Cathode (-) | Anode (+) | Electrochemical setup | Solvent | Electrolyte | Catalyst/Additive | Product | Yield (%) | Ref. | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Aryl halides | |||||||||||||||||
Aryl bromide | Ag | Mg | undivided cell | DMF | nBu4NI | CH3I | methyl benzyl ester | 30-78 | [ | ||||||||
Dibromobenzene | Ag | Mg | undivided cell | DMF | Et4NBF4 | — | benzene dicarboxylic acid | 49-71 | [ | ||||||||
4-Iodobenzonitrile | Ag | Ag | undivided cell | DMF | nBu4NBF4 | — | 4-cyanobenzoic acid | 40-90 | [ | ||||||||
Aryl halides | SS | Sm | undivided Cell | DMF | nBu4NBF4 | — | benzoic acid | 42-80 | [ | ||||||||
Bromospiropyran | GC or Ag | Pt | undivided cell | DMF | nBu4NPF6 | CH3I | methyl carboxylated spiropyran | 35 | [ | ||||||||
Benzyl halides | |||||||||||||||||
Benzyl chloride | Ag | Al | undivided cell | MeCN | Et4NClO4 | — | phenylacetic acid | 79-95 | [ | ||||||||
Benzyl halides | Pt | Pt | quasi-divided cell | DMF | nBu4NBF4 | — | N-methyl-N-(phenylac etoxy)methylforamides | 69-78 | [ | ||||||||
Benzyl bromide | mesoporous Ag | Mg | undivided cell | DMF | Et4NBr | CH3I for ester formation | methyl ester | 78 | [ | ||||||||
4-Nitrobenzyl bromide | Cu/Pd/rGO/GCE | Pt | undivided cell | CH3CN | nBu4NPF6 | nanoparticles/ Pd nanoparticles/ reduced graphene oxide nanocomposite | 4-nitrophenylacetic acid | 76 | [ | ||||||||
Secondary benzyl chloride | Ag foil | Ag foil | undivided cell | bis(tri-fluoromethanesulfonyl)imide (PP13 TFSI) | bis(tri-fluoromethanesulfonyl)imide (PP13 TFSI) | — | ibuprofen | 83 | [ | ||||||||
α-Methylbenzyl bromide | Ag | Pt | divided cell | CH3CN (cathodic side), aqueous (anodic side) | nBu4NI (catholyte), KHCO3 (anolyte) | paired electrolysis | phenylacetic acid | 86 | [ | ||||||||
Secondary benzyl halide | Sm | SS | undivided Cell | CH3CN | nBu4NI | Sm(II) generated pre-electrolysis | carboxylic acid | 42-96 | [ | ||||||||
Secondary benzyl bromide | Co@Ag | Mg | undivided Cell | CH3CN | nBu4NI | encapsulated Co(salen) (Co@Ag) | chiral carboxylic acid | 58 | [ | ||||||||
Substrate | Cathode (-) | Anode (+) | Electrochemical setup | Solvent | Electrolyte | Catalyst/Additive | Product | Yield (%) | Ref. | ||||||||
Unactivated halides | |||||||||||||||||
Aliphatic, benzyl, and aryl halide | Ag | Pt | undivided cell | DMF | nBu4NBr | MgBr2 added to prevent ester formation | carboxylic acid | 41‒78 | [ | ||||||||
Unactivated Alkyl Bromides, Unactivated aryl halides, aryl sulfonates | C felt | C or Zn | undivided and divided cell | NMP | NaI | Ni with bpy ligands, oxidative chlorination of tolene as paired oxidation reaction, KOtBu, DMAP, MgBr2 | carboxylic acid | 27‒83 | [ | ||||||||
Allylic halides | |||||||||||||||||
Allylic chloride | Ni Foam | Mg | undivided cell | DMF | nBu4NPF6 | Co(OAc)2 PPh3 | carboxylic acid | 45‒79 | [ | ||||||||
Allylic chloride | Ag | Mg | undivided cell | DMF | nBu4NI | Ni(dppm)Cl2 | carboxylic acid | 43‒96 | [ | ||||||||
Cinnamyl chloride | Cu@Ag | Mg | undivided cell | CH3CN | nBu4NI | encapsulated Cu(salen) (Cu@Ag) | carboxylic acid | 37‒99 | [ | ||||||||
Pseudo halides and others | |||||||||||||||||
4-nitrobenzyl phenyl thioether | GC | Pt | undivided cell | DMF | nBu4NBF4 | — | 4-aminophenyl acetic acid (from C-S cleavage) | 10 | [ | ||||||||
Homostyrenyl acetate | Pt | Mg | undivided cell | EtOH | Et4NOTs | Pd, DPPPh, 1,2-(bis(diphenylphosphino)benzene) | carboxylic acid with 20:1 branched to linear ratio | 58‒95 | [ | ||||||||
Cinnamyl Aacetate | Pt | Mg | undivided cell | EtOH | Et4NOTs | Pd, (R)-MeO-BIPHME (chiral bidentate triarylphosphine) | carboxylic acid 67% ee | 55‒66 | [ | ||||||||
Benzal diacetate | Pt | Mg | undivided cell | DMF | nBu4NBF4 | — | mandelic acid | 61‒97 | [ | ||||||||
Allylic acetate | C | Mg | undivided cell | DMF | nBu4NBF4 | Ni(bpy)2Br2, CH3I and K2CO3 | unsaturated carboxylic acid | 30‒71 | [ | ||||||||
Primary and secondary benzylic C-N bonds in benzylammonium | C | Pt | undivided cell | DMF | nBu4PBF4 | trimethylammonia generated in situ as sacrificial reductant | carboxylic acid | 25‒87 | [ | ||||||||
Organic sulfones | Pt | Mg | undivided cell | DMF | nBu4NI | triethanolamine as proton source | phenylacetic acid | 73‒99 | [ | ||||||||
N-Boc-α-amino sulfones | Pt | Mg | undivided cell | DMF | nBu4NBF4 | — | N-boc-α-amino acids | 58‒87 | [ | ||||||||
Aromatic alcohol | Ni | Glassy carbon | undivided cell | CH3CN | tetraethylammonium acetate (TEAAc) | TEMPO as the redox mediator that oxidize alcohol to ketone | α-hydroxy acid | 61 | [ |
Table 1 Electrocarboxylation Conditions of Aryl Halides, Benzyl Halides, Allylic Halides, and Pseudohalides.
Substrate | Cathode (-) | Anode (+) | Electrochemical setup | Solvent | Electrolyte | Catalyst/Additive | Product | Yield (%) | Ref. | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Aryl halides | |||||||||||||||||
Aryl bromide | Ag | Mg | undivided cell | DMF | nBu4NI | CH3I | methyl benzyl ester | 30-78 | [ | ||||||||
Dibromobenzene | Ag | Mg | undivided cell | DMF | Et4NBF4 | — | benzene dicarboxylic acid | 49-71 | [ | ||||||||
4-Iodobenzonitrile | Ag | Ag | undivided cell | DMF | nBu4NBF4 | — | 4-cyanobenzoic acid | 40-90 | [ | ||||||||
Aryl halides | SS | Sm | undivided Cell | DMF | nBu4NBF4 | — | benzoic acid | 42-80 | [ | ||||||||
Bromospiropyran | GC or Ag | Pt | undivided cell | DMF | nBu4NPF6 | CH3I | methyl carboxylated spiropyran | 35 | [ | ||||||||
Benzyl halides | |||||||||||||||||
Benzyl chloride | Ag | Al | undivided cell | MeCN | Et4NClO4 | — | phenylacetic acid | 79-95 | [ | ||||||||
Benzyl halides | Pt | Pt | quasi-divided cell | DMF | nBu4NBF4 | — | N-methyl-N-(phenylac etoxy)methylforamides | 69-78 | [ | ||||||||
Benzyl bromide | mesoporous Ag | Mg | undivided cell | DMF | Et4NBr | CH3I for ester formation | methyl ester | 78 | [ | ||||||||
4-Nitrobenzyl bromide | Cu/Pd/rGO/GCE | Pt | undivided cell | CH3CN | nBu4NPF6 | nanoparticles/ Pd nanoparticles/ reduced graphene oxide nanocomposite | 4-nitrophenylacetic acid | 76 | [ | ||||||||
Secondary benzyl chloride | Ag foil | Ag foil | undivided cell | bis(tri-fluoromethanesulfonyl)imide (PP13 TFSI) | bis(tri-fluoromethanesulfonyl)imide (PP13 TFSI) | — | ibuprofen | 83 | [ | ||||||||
α-Methylbenzyl bromide | Ag | Pt | divided cell | CH3CN (cathodic side), aqueous (anodic side) | nBu4NI (catholyte), KHCO3 (anolyte) | paired electrolysis | phenylacetic acid | 86 | [ | ||||||||
Secondary benzyl halide | Sm | SS | undivided Cell | CH3CN | nBu4NI | Sm(II) generated pre-electrolysis | carboxylic acid | 42-96 | [ | ||||||||
Secondary benzyl bromide | Co@Ag | Mg | undivided Cell | CH3CN | nBu4NI | encapsulated Co(salen) (Co@Ag) | chiral carboxylic acid | 58 | [ | ||||||||
Substrate | Cathode (-) | Anode (+) | Electrochemical setup | Solvent | Electrolyte | Catalyst/Additive | Product | Yield (%) | Ref. | ||||||||
Unactivated halides | |||||||||||||||||
Aliphatic, benzyl, and aryl halide | Ag | Pt | undivided cell | DMF | nBu4NBr | MgBr2 added to prevent ester formation | carboxylic acid | 41‒78 | [ | ||||||||
Unactivated Alkyl Bromides, Unactivated aryl halides, aryl sulfonates | C felt | C or Zn | undivided and divided cell | NMP | NaI | Ni with bpy ligands, oxidative chlorination of tolene as paired oxidation reaction, KOtBu, DMAP, MgBr2 | carboxylic acid | 27‒83 | [ | ||||||||
Allylic halides | |||||||||||||||||
Allylic chloride | Ni Foam | Mg | undivided cell | DMF | nBu4NPF6 | Co(OAc)2 PPh3 | carboxylic acid | 45‒79 | [ | ||||||||
Allylic chloride | Ag | Mg | undivided cell | DMF | nBu4NI | Ni(dppm)Cl2 | carboxylic acid | 43‒96 | [ | ||||||||
Cinnamyl chloride | Cu@Ag | Mg | undivided cell | CH3CN | nBu4NI | encapsulated Cu(salen) (Cu@Ag) | carboxylic acid | 37‒99 | [ | ||||||||
Pseudo halides and others | |||||||||||||||||
4-nitrobenzyl phenyl thioether | GC | Pt | undivided cell | DMF | nBu4NBF4 | — | 4-aminophenyl acetic acid (from C-S cleavage) | 10 | [ | ||||||||
Homostyrenyl acetate | Pt | Mg | undivided cell | EtOH | Et4NOTs | Pd, DPPPh, 1,2-(bis(diphenylphosphino)benzene) | carboxylic acid with 20:1 branched to linear ratio | 58‒95 | [ | ||||||||
Cinnamyl Aacetate | Pt | Mg | undivided cell | EtOH | Et4NOTs | Pd, (R)-MeO-BIPHME (chiral bidentate triarylphosphine) | carboxylic acid 67% ee | 55‒66 | [ | ||||||||
Benzal diacetate | Pt | Mg | undivided cell | DMF | nBu4NBF4 | — | mandelic acid | 61‒97 | [ | ||||||||
Allylic acetate | C | Mg | undivided cell | DMF | nBu4NBF4 | Ni(bpy)2Br2, CH3I and K2CO3 | unsaturated carboxylic acid | 30‒71 | [ | ||||||||
Primary and secondary benzylic C-N bonds in benzylammonium | C | Pt | undivided cell | DMF | nBu4PBF4 | trimethylammonia generated in situ as sacrificial reductant | carboxylic acid | 25‒87 | [ | ||||||||
Organic sulfones | Pt | Mg | undivided cell | DMF | nBu4NI | triethanolamine as proton source | phenylacetic acid | 73‒99 | [ | ||||||||
N-Boc-α-amino sulfones | Pt | Mg | undivided cell | DMF | nBu4NBF4 | — | N-boc-α-amino acids | 58‒87 | [ | ||||||||
Aromatic alcohol | Ni | Glassy carbon | undivided cell | CH3CN | tetraethylammonium acetate (TEAAc) | TEMPO as the redox mediator that oxidize alcohol to ketone | α-hydroxy acid | 61 | [ |
Substrate | Cathode (-) | Anode (+) | Electrochemical Setup | Solvent | Electrolyte | Catalysts/Additives | Product | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|---|
Alkenes | |||||||||
Aryl substituted alkenes | Ni | Al | undivided cell | DMF | nBu4NBr | — | dicarboxylic acid (aryl succinic acid) | 50-87 | [ |
Cinnamate esters | Ti | Mg | undivided cell | CH3CN | Et4NF4 | — | mono and dicarboxylic acids | 61-77 | [ |
Alkene and alkyl bromide | Graphite | Mg | undivided cell | DMF | nBu4NPF6 | — | carboxylic acid | 38-79 | [ |
Conjugated dienes and poly aromatics | |||||||||
Conjugated dienes | SS | C | undivided cell | DMF | Et4NI | triethanolamine or water as proton source | α,δ-hydrocarboxylic acid | 30-60 | [ |
Polycyclic aromatic hydrocarbon | Ni | Al | undivided cell | DMF | nBu4NBr | — | trans-dicarboxylic acid | 55-92 | [ |
Heteroaromatics | Pt | Mg | undivided cell | DMF | nBu4NCIO4 | — | trans-oriented 2,3-dicarboxylic acids | 44-98 | [ |
Styrenes | |||||||||
Styrene | Ni | Mg | undivided cell | DMF | nBu4NBF4 | H2O as proton source | β-substituted carboxylic acid (major), dicarboxylic acid (minor) | 27-60 | [ |
Styrene | nitrogen- coordinated single-atomic Cu catalyst | Mg | undivided cell | CH3CN | nBu4NBr | — | dicarboxylic acid | — | [ |
trans-Stillbene | Si Nanowires | Al | undivided cell | CH3CN | nBu4NBr | photoelectrochemical condition | carboxylic acid | — | [ |
α,β-Unsaturated compounds | |||||||||
α,β-Unsaturated ester | C | C | undivided cell | DMF | Et4NI | triethanolamine as reductant and proton source | β-carboxylated ester | 23-81 | [ |
α,β-Unsaturated ketone | Si nanowires | Al | undivided cell | CH3CN | nBu4NBr | photoelectrochemical condition | β-carboxyketone | 65-98 | [ |
Fluoro-substituted alkenes | |||||||||
Alkene with α-CF3 group | Pt | Pt | undivided cell | DMF | nBu4NClO4 | — | defluoronative γ-carboxylation, vinyl acetic acid | 40-83 | [ |
gem-difluoroalkenes | Pt | Ni | undivided cell | DMF | nBu4NI | — | α-fluoroacrylic acid (defluorinative carboxylation) | 35-76 | [ |
Table 2 Electrocarboxylation Conditions of Alkenes and Derivatives.
Substrate | Cathode (-) | Anode (+) | Electrochemical Setup | Solvent | Electrolyte | Catalysts/Additives | Product | Yield (%) | Ref. |
---|---|---|---|---|---|---|---|---|---|
Alkenes | |||||||||
Aryl substituted alkenes | Ni | Al | undivided cell | DMF | nBu4NBr | — | dicarboxylic acid (aryl succinic acid) | 50-87 | [ |
Cinnamate esters | Ti | Mg | undivided cell | CH3CN | Et4NF4 | — | mono and dicarboxylic acids | 61-77 | [ |
Alkene and alkyl bromide | Graphite | Mg | undivided cell | DMF | nBu4NPF6 | — | carboxylic acid | 38-79 | [ |
Conjugated dienes and poly aromatics | |||||||||
Conjugated dienes | SS | C | undivided cell | DMF | Et4NI | triethanolamine or water as proton source | α,δ-hydrocarboxylic acid | 30-60 | [ |
Polycyclic aromatic hydrocarbon | Ni | Al | undivided cell | DMF | nBu4NBr | — | trans-dicarboxylic acid | 55-92 | [ |
Heteroaromatics | Pt | Mg | undivided cell | DMF | nBu4NCIO4 | — | trans-oriented 2,3-dicarboxylic acids | 44-98 | [ |
Styrenes | |||||||||
Styrene | Ni | Mg | undivided cell | DMF | nBu4NBF4 | H2O as proton source | β-substituted carboxylic acid (major), dicarboxylic acid (minor) | 27-60 | [ |
Styrene | nitrogen- coordinated single-atomic Cu catalyst | Mg | undivided cell | CH3CN | nBu4NBr | — | dicarboxylic acid | — | [ |
trans-Stillbene | Si Nanowires | Al | undivided cell | CH3CN | nBu4NBr | photoelectrochemical condition | carboxylic acid | — | [ |
α,β-Unsaturated compounds | |||||||||
α,β-Unsaturated ester | C | C | undivided cell | DMF | Et4NI | triethanolamine as reductant and proton source | β-carboxylated ester | 23-81 | [ |
α,β-Unsaturated ketone | Si nanowires | Al | undivided cell | CH3CN | nBu4NBr | photoelectrochemical condition | β-carboxyketone | 65-98 | [ |
Fluoro-substituted alkenes | |||||||||
Alkene with α-CF3 group | Pt | Pt | undivided cell | DMF | nBu4NClO4 | — | defluoronative γ-carboxylation, vinyl acetic acid | 40-83 | [ |
gem-difluoroalkenes | Pt | Ni | undivided cell | DMF | nBu4NI | — | α-fluoroacrylic acid (defluorinative carboxylation) | 35-76 | [ |
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