Chiral electroorganic chemistry: An interdisciplinary research across electrocatalysis and asymmetric synthesis

Xue, Yan-Fang; Ge, Qingmei; Liu, Mao; Cong, Hang; Tao, Zhu

doi:10.1016/j.mcat.2020.111296

Cited by 17 publications

(8 citation statements)

References 127 publications

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“…The use of chiral electrocatalysts to produce enantiopure products has gained particular attention in recent years. One approach derives directly from the surface modification methodology discussed in the previous section, where a reversibly adsorbing chiral modifier is added to the solution to promote the formation of a weak adduct with the reactant that, when bound to the surface, forces a particular stereochemistry thanks to the resulting chiral environment. ,, In an early example of this, the electrochemical reduction of 4-methylcoumarin and 5-methoxy-4-methylcoumarin in the presence of optically active amines was shown to afford optically active dihydrocoumarins . The synthesis of 2-hydroxy-2-phenylpropionic acid (atrolactic acid) from acetophenone via CO 2 electrocatalytic fixation could be made enantioselective, to produce either the (R) or the (S) enantiomer, by adding cinchonidine or cinchonine to the solution, respectively .…”

Section: Adsorbates As Co-catalysts or Catalyst Modifiersmentioning

confidence: 99%

Designing Sites in Heterogeneous Catalysis: Are We Reaching Selectivities Competitive With Those of Homogeneous Catalysts?

Zaera

2022

Chem. Rev.

207

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A critical review of different prominent nanotechnologies adapted to catalysis is provided, with focus on how they contribute to the improvement of selectivity in heterogeneous catalysis. Ways to modify catalytic sites range from the use of the reversible or irreversible adsorption of molecular modifiers to the immobilization or tethering of homogeneous catalysts and the development of well-defined catalytic sites on solid surfaces. The latter covers methods for the dispersion of single-atom sites within solid supports as well as the use of complex nanostructures, and it includes the post-modification of materials via processes such as silylation and atomic layer deposition. All these methodologies exhibit both advantages and limitations, but all offer new avenues for the design of catalysts for specific applications. Because of the high cost of most nanotechnologies and the fact that the resulting materials may exhibit limited thermal or chemical stability, they may be best aimed at improving the selective synthesis of high value-added chemicals, to be incorporated in organic synthesis schemes, but other applications are being explored as well to address problems in energy production, for instance, and to design greener chemical processes. The details of each of these approaches are discussed, and representative examples are provided. We conclude with some general remarks on the future of this field.

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Section: Adsorbates As Co-catalysts or Catalyst Modifiersmentioning

confidence: 99%

Designing Sites in Heterogeneous Catalysis: Are We Reaching Selectivities Competitive With Those of Homogeneous Catalysts?

Zaera

2022

Chem. Rev.

207

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“…477 An even more recent review has been published but this interdisciplinary field still remains a matter of specialists. 478 3.5.4. enynes has been investigated by Lin, Liu, and co-workers. 479 As shown in Scheme 218, the 1,2-adduct also affords an allene through 1,3-proton shift.…”

Section: Cascade Involving Addition To Alkenesmentioning

confidence: 99%

“…The reader is referred to this article for further developments . An even more recent review has been published but this interdisciplinary field still remains a matter of specialists …”

Section: Chiral Transition-metal-catalyzed Asymmetric Radical Processesmentioning

confidence: 99%

Enantioselective Radical Reactions Using Chiral Catalysts

Mondal¹,

et al. 2022

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Scheme 24 Enantioselective Radical Hydroacylation of Enals with α-Ketoacids byMerging Photoredox Catalysis with Amine Catalysis.Jang et al. exploited enantioselective tandem Michael addition/oxyamination of α,β-unsaturated aldehydes by combining asymmetric iminium catalysis using organocatalyst with photoinduced SOMO catalysis using N719/TiO2. 60 Here, TiO2 acts as a second cooperative photocatalyst along with Ru photocatalyst N719 which bound to the latter, increases the enantio-and diastereoselectivity of the process. Adamantane carboxylic acid (30 mol%) was used as an additive which promotes formation of iminium ion 2.1.48A from aldehyde 2.1.48 and chiral amine catalyst. This iminium intermediate then reacts with diethyl malonate to provide intermediate 2.1.48B which either undergoes hydrolysis to form β-substituted aldehyde 2.1.50 or photo-oxidation by the photoexcited Ru(II) dye to form enamine radical 2.1.48C. Subsequent addition of TEMPO to radical intermediate 2.1.48BC followed by hydrolysis afforded the desired product 2.1.49 (Scheme 25). This mechanism is obeying to a polar/radical crossover sequence where the first stereocontrol arises from the addition of the malonate.Recently, Bach group reported promising preliminary results of enantioselective [2+2] photocycloaddition of cinnamaldehyde in the presence of ruthenium photocatalyst and proline derived organocatalyst. 61

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“…Organic electrochemical synthesis has been utilized to achieve the C-H activation/annulation, [22][23][24][25] the construction of polycyclic aza-fused arenes [26][27][28][29] and polycyclic S-containing arenes, 30 and the electrochemical transformation of phosphorus compounds have also been reported. [31][32][33] With our continuous interests in electrochemistry [34][35][36][37][38][39] and multiple C-H activations and annulation 19,40 , herein, we report a versatile electrochemical oxidative method under oxidant-free conditions to produce fused polycyclic phosphonium salts via the C-H activation/annulation of aryl phosphine compounds (Scheme 1d), and metals and oxidants could be readily avoided in this strategy.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical oxidative intramolecular annulation of aryl phosphine compounds: an efficient approach for synthesizing π-conjugated phosphonium salts

et al. 2023

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Chiral electroorganic chemistry: An interdisciplinary research across electrocatalysis and asymmetric synthesis

Cited by 17 publications

References 127 publications

Designing Sites in Heterogeneous Catalysis: Are We Reaching Selectivities Competitive With Those of Homogeneous Catalysts?

Designing Sites in Heterogeneous Catalysis: Are We Reaching Selectivities Competitive With Those of Homogeneous Catalysts?

Enantioselective Radical Reactions Using Chiral Catalysts

Electrochemical oxidative intramolecular annulation of aryl phosphine compounds: an efficient approach for synthesizing π-conjugated phosphonium salts

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