Electrochemical Dearomative Halocyclization of Tryptamine and Tryptophol Derivatives

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 38(10), P. 1070 - 1074

Published: April 28, 2020

Summary of main observation and conclusion Owing to the easy functionalization 3‐haloindolines many biologically active compounds, extensive efforts have been made for their efficient preparation. Herein, an electrochemical dearomative bromo‐ chloro‐cyclization tryptamine tryptophol derivatives has developed under undivided electrolytic conditions. In this protocol, neither external chemical oxidants nor harsh conditions are needed, a wide range substituted hexahydropyrroloindolines/tetrahydrofuroindolines obtained with halide ion in high efficiencies. Moreover, electrolysis could also be scaled up gram synthesis good yields.

Language: Английский

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Electrooxidative B−H Functionalization of nido‐Carboranes

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(14), P. 7838 - 7844

Published: Dec. 29, 2020

Abstract An atom‐economical method for the direct B−H functionalization of nido ‐carboranes (7,8‐ ‐C 2 B 9 H 12 − ) has been developed under electrochemical reaction conditions. In this system, anodic oxidation serves as a green alternative traditional chemical oxidants in ‐carboranes. No transition‐metal catalyst is required and different heteroatoms bearing lone pair are reactive transformation. Coupling with thioethers, selenides, tellurides, N‐heterocycles, phosphates, phosphines, arsenides antimonides demonstrates high site‐selectivity efficiency. Importantly, can be easily incorporated into drug motifs through protocol.

Language: Английский

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Phosphorylation of arenes, heteroarenes, alkenes, carbonyls and imines by dehydrogenative cross-coupling of P(O)–H and P(R)–H

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 20(3), P. 498 - 537

Published: Nov. 23, 2021

Organophosphorous compounds have recently emerged as a powerful class of with widespread applications, such in bioactive natural products, pharmaceuticals, agrochemicals and organic materials, ligands catalysis. The preparation these requires synthetic techniques novel catalytic systems varying from transition metal, photo- electrochemical catalysis to transformations without metal catalysts. Over the past few decades, addition P-H bonds alkenes, alkynes, arenes, heteroarenes other unsaturated substrates hydrophosphination related reactions via above-mentioned processes has an atom economical approach obtain organophosphorus compounds. In most cycles, bond is cleaved yield phosphorus-based radical, which adds onto substrate followed by reduction corresponding radical yielding product.

Language: Английский

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S-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12311 - 12318

Published: Aug. 16, 2023

Dithiocarbamates synthesis is extremely important in plenty of biomedical and agrochemical applications, especially fungicide development, but remains a great challenge. In this work, we have successfully developed multicomponent reaction protocol to convert H2S into S-alkyl dithiocarbamates under constant current conditions. No additional oxidants nor catalysts are required, due mild conditions, the reactions display broad substrate scope, including varieties thiols or disulfides.

Language: Английский

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Electrochemical Enabled Cascade Phosphorylation of N−H/O−H/S−H Bonds with P−H Compounds: An Efficient Access to P(O)‐X Bonds

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(60), P. 14931 - 14935

Published: Aug. 27, 2021

An electrochemical three component cascade phosphorylation reaction of various heteroatoms-containing nucleophiles including carbazoles, indoles, phenols, alcohols, and thiols with Ph2 PH has been established. Electricity is used as the "traceless" oxidant water air are utilized "green" oxygen source. All kinds structurally diverse organophosphorus compounds P(O)-N/P(O)-O/P(O)-S bonds assembled in moderate to excellent yields (three categories products, 50 examples, up 97 % yield). A tentative free radical course put forward rationalize procedure.

Language: Английский

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Electrooxidation‐Induced C(sp³)–H/C(sp²)–H Radical‐Radical Cross‐Coupling between Xanthanes and Electron‐Rich Arenes

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(12), P. 1422 - 1428

Published: March 15, 2022

Comprehensive Summary The arylation of C(sp 3 ) − H bonds has been a priority research topic in organic synthesis. Minsici reactions have the powerful methods for 2 formation. Despite its mature development, scopes arenes are usually suitable electron‐deficient heterocyclic compounds, rather than electron‐rich arenes. Herein, we report an electrooxidation‐induced alkylation with evolution under exogenous oxidant‐free conditions, avoiding utilization metal catalysts. This protocol is well performed various aniline derivatives and nitrogen‐containing compounds. We anticipate that this electro‐oxidative represents important expansion classic alkylation, thereby proving attractive strategy developments radical cross‐coupling chemistry.

Language: Английский

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Hydrophosphorylation of electron-deficient alkenes and alkynes mediated by convergent paired electrolysis

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(59), P. 8238 - 8241

Published: Jan. 1, 2022

A straightforward and practical strategy for hydrophosphorylation of electron-deficient alkenes alkynes to access γ-ketophosphine oxides, enabled by CPE in the absence a metal, base, redox reagent, has been described.

Language: Английский

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Electrochemical Oxidation‐Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(16), P. 2735 - 2740

Published: July 1, 2022

Abstract A metal‐ and exogenous‐oxidant‐free oxidation‐induced oxyphosphorylation of alkenes alkynes with water for β‐ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible a wide range alkenes, alkynes, diarylphosphorus derivatives, enables gram‐scale synthesis β‐ketophosphonates. The mechanistic study revealed that P radicals were generated via hydrogen atom transfer (HAT) event jointly mediated by tetrabutylammonium acetate anode oxidation process. magnified image

Language: Английский

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NHPI/O₂‐Mediated Electrochemical Intermolecular Cyclization/Dehydrogenation for the Construction of Polycyclic Quinazolinones

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2248 - 2254

Published: May 27, 2023

Abstract Herein, an eco‐friendly and atom‐economical electrochemical methodology with isatins 1,2,3,4‐tetrahydroisoquinolines through NHPI/O 2 ‐mediated intermolecular oxidation/annulation is disclosed, leading to a variety of polycyclic quinazolinones in 46–82% yields. This oxidative cyclization proceeded transition metal‐ strong oxidant‐free conditions generated H CO as byproducts. Additionally, late‐stage functionalization broad substrate scope demonstrated the synthetic usefulness this protocol.

Language: Английский

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Studies on the electrochemical reactions of 1-amino phosphonates

Electrochemistry Communications, Journal Year: 2025, Volume and Issue: unknown, P. 107944 - 107944

Published: May 1, 2025

Language: Английский

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