Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones

Wang, Huiqiao; Zhang, Jinjin; Tan, Jiajing; Xin, Lilan; Li, Yaping; Zhang, Sheng; Xu, Kun

doi:10.1021/acs.orglett.8b00165

Cited by 70 publications

(20 citation statements)

References 61 publications

(29 reference statements)

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“…Trisubstituted 2‐oxazolines are key structural motifs that are found in many pharmaceutical relevant compounds [25,26] . In 2018, we reported an electrochemical cyclization for the synthesis of trisubstituted 2‐oxazolines with KI as the mediator [27] . As shown in Scheme 32, the cyclization reaction was carried out in an undivided cell equipped with platinum electrodes with CH 3 CN/MeOH as the mixed solvent under CCE conditions.…”

Section: Halogen As the Inner‐sphere Et Mediatorsmentioning

confidence: 99%

Indirect Electrosynthesis with Halogen Ions as Mediators

Lian

Zeng

2021

The Chemical Record

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Organic electrosynthesis has gained increasing research interest as it harvests electric current as redox regents, thereby providing a sustainable alternative to conventional approaches. Compared with direct electrosynthesis, indirect electrosynthesis employs mediator(s) to lower the overpotentials for substrate activation, and enhance the reaction efficiency and functional group compatibility by shifting the heterogenous electron transfer process to be homogenous. As one of the most versatile and cost‐efficient mediators, halogen mediators are always combined with an irreversible halogenation reaction. Thus, the electrochemical reaction between halogen mediators and substrates doesn't directly controlled by the two standard potentials difference. In this account, our recent developments in the area of halogen‐mediated indirect electrosynthesis are summarized. The anodically generated halogen species from halogenide salts have the abilities to undergo electron‐transfer (ET) or hydrogen‐atom‐ transfer (HAT) processes. The reaction features, scopes, limitations, and mechanistic rationalisations are discussed in this account. We hope our studies will contribute to the future developments to broaden the scope of halogen‐mediated electrosynthesis.

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Section: Halogen As the Inner‐sphere Et Mediatorsmentioning

confidence: 99%

Indirect Electrosynthesis with Halogen Ions as Mediators

Lian

Zeng

2021

The Chemical Record

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“…In 2018, Wang and co-workers 26 reported on a synthesis of trisubstituted oxazolines 50 with excellent yield via the dehydrogenative cyclization of -amino aryl ketones 49 (Scheme 28). The cyclization was performed under constant current conditions in an undivided cell equipped with a Pt anode and a Pt cathode using KI as both supporting electrolyte and catalyst.…”

Section: Oxazolesmentioning

confidence: 99%

Recent Advances in Electrochemistry for the Synthesis of N-Heterocycles

Sbei¹,

Listratova²,

Титов³

et al. 2019

Synthesis

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The construction of N-heterocyclic rings represents a very important and fast-developing area of organic synthesis. In this context, electrochemistry has emerged as a mild solution for generating in situ the required electrophilic substrates, bases and nucleophiles derived from low-level and extremely stable reagents, the further application of which makes some heterocycles more accessible. In this review, we have covered the recent advances in the electrochemical synthesis of five- and six-membered N-heterocyclic compounds published from 2017 to October 2018.1 Introduction2 Electrochemical Synthesis of Five-Membered N-Containing Heterocycles2.1 Pyrrolidines2.2 Imidazoles2.3 Pyrazoles2.4 Triazoles2.5 Oxazoles2.6 Indoles2.7 Thiazoless3 Electrochemical Synthesis of Six-Membered N-Containing Heterocycles3.1 Piperidines and Pyridines3.2 Quinazolinones3.3 Benzoxazines4 Conclusions

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“…Recently, Zhang and Xu reported an electrochemical dehydrogenative cyclization of β‐aminoaryl ketones 116 to yield trisubstituted 2‐oxazolines 117 (Scheme ) . With cheap KI as the catalyst and electrolyte, diverse trisubstituted 2‐oxazolines were constructed in good to excellent yields.…”

Section: α‐C–x Bond Formation From In Situ Electrogenerated α‐Halogenmentioning

confidence: 99%

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

Liang

Zeng

et al. 2018

Adv Synth Catal

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The α‐C–H functionalization of carbonyl compounds represents a cornerstone of organic chemistry. Site‐selective α‐C−H bond functionalization of carbonyl compounds to afford more versatile functionalized groups has become a promising strategy for atom‐economical C−C and C−X bond formation. Organic electrosynthesis is revolutionizing the nature of organic synthesis, and this field has seen explosive growth in recent years. In this review, we discuss advances in the use of electrochemistry for the α‐C–H oxidative functionalization of carbonyl compounds published since 2000.

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Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones

Cited by 70 publications

References 61 publications

Indirect Electrosynthesis with Halogen Ions as Mediators

Indirect Electrosynthesis with Halogen Ions as Mediators

Recent Advances in Electrochemistry for the Synthesis of N-Heterocycles

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

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