Recent Advances in the Electrochemical α‐C–H Bond Functionalization of Carbonyl Compounds

Liang, Shuhua; Xu, Kun; Zeng, Cheng‐Chu; Tian, Hongyu; Sun, Baoguo

doi:10.1002/adsc.201800519

Cited by 88 publications

(19 citation statements)

References 108 publications

(61 reference statements)

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“…While electrochemical organic synthesis has a long history, it has recently attracted increasing interest due to its mildness, atom economy, and efficiency . Normal organic reactions, especially oxidation or reduction, require stoichiometric amounts of reagents and discharge of the same amount of waste.…”

Section: Introductionmentioning

confidence: 99%

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

et al. 2021

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Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

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Section: Introductionmentioning

confidence: 99%

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

et al. 2021

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“…Based on our mechanistic findings, [13,23] we propose a tentative mechanism as depicted in Scheme 4. First, the carbanion 5 was generated via the deprotonation of the acidic α‐C(sp 3 )−H as well as a transesterification [20] process assisted by bases.…”

Section: Resultsmentioning

confidence: 87%

Access to 10‐Phenanthrenols via Electrochemical C−H/C−H Arylation

et al. 2020

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A protocol for the synthesis of 10‐phenanthrenol from 1‐biphenyl‐2‐ylethanone bearing an electron‐withdrawing group through metal‐ and oxidant‐free C−H/C−H arylation has been established. The electrochemical intramolecular cycloaromatization avoids the use of excess amounts of chemical oxidizing agents, and provides concise and regio‐selective access to a variety of valuable 10‐phenanthrenol derivatives.

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“…Nucleophiles produced in situ by blending a base and dynamic C-H or heteroatom-H compound straightforwardly coupled with different organic halides. [3][4][5] The strategy seems to have a preferred critical position in that it can do without planning of organometallic reagents. In 1975, Cassar and Heck revealed a palladium-catalyzed cross-coupling reaction of acetylides, produced inside the reaction mixture terminal alkynes and sodium methoxide or trimethylamine (TMA), with aryl halides.…”

Section: Introductionmentioning

confidence: 99%

Markovnikov versus anti‐Markovnikov addition and C–H activation: Pd–Cu synergistic catalysis

Ullah

Thomas²

2020

Applied Organom Chemis

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Copper-and palladium-mediated transmetalation and coupling reactions are the backbone to several synthetic methodologies in organic chemistry for CC bond formation. Computer-aided simulations using density functional theory (DFT) (B3LYP-D3 functional with 6-31G** and effective core potential (ECP)-LACVP** for heavy atoms for optimizations and cc-pVTZ(−f) and ECP-LACV3P** for single-point calculations) was used to shed light on the probable mechanism of a novel synergistic Cu/Pd catalysts for the coupling of alkene, (Bpin)2 (where, pin = pinacolate), and vinyl-or aryl-halogenated analogues. Every single conceivable pathway was carefully contemplated, and the base minimum energy pathway was found effectively. The copper-catalyzed nucleophilic generation yields anti-Markovnikov product using styrene as an alkene. This study affirms quantitatively and accurately how the reaction proceeds and at which steps of the synergistic catalysis the demand of the transmetalation and nucleophile formation for the CC coupling using phosphine ligands arise. We conclude that the E and Z selectivity depends on the stereochemistry of the substrates used.

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Recent Advances in the Electrochemical α‐C–H Bond Functionalization of Carbonyl Compounds

Cited by 88 publications

References 108 publications

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Access to 10‐Phenanthrenols via Electrochemical C−H/C−H Arylation

Markovnikov versus anti‐Markovnikov addition and C–H activation: Pd–Cu synergistic catalysis

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