Research progress in electrochemical/photochemical utilization of methanol as a C1 source

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8313 - 8327

Опубликована: Янв. 1, 2023

This review highlights the recent advances in various electrochemical and photochemical reactions using methanol as a sustainable C1 source.

Язык: Английский

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Recent Advances in Cyclization Reactions of 1,6‐Enynes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1220 - 1268

Опубликована: Янв. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Язык: Английский

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Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions

Molecules, Год журнала: 2023, Номер 28(7), С. 3027 - 3027

Опубликована: Март 28, 2023

Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction functional groups. In radical difunctionalization reactions, radicals first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, ring opening. The resulting undertake following paths second functionalization: (1) couple with other groups, (2) oxidize to cations then react nucleophiles, (3) reduce anions electrophiles, (4) metal-complexes. rearrangements provide opportunity 1,3-, 1,4-, 1,5-, 1,6-, 1,7-difunctionalization products. Multiple ways initiate reaction coupling intermediate make reactions good at remote positions. These offer advantages synthetic efficiency, operation simplicity, product diversity.

Язык: Английский

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Electrocatalytic Annulation–Iodosulfonylation of Indole‐Tethered 1,6‐Enynes to Access Pyrrolo[1,2‐a]indoles

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(10)

Опубликована: Янв. 9, 2024

Abstract We present the first example of electrocatalytic three‐component annulation–iodosulfonylation indole‐tethered 1,6‐enynes with arylsulfonyl hydrazides and KI for accessing various iodosulfonated pyrrolo[1,2‐ a ]indoles in moderate to excellent yields high stereospecificity. This electrosynthesis opens new avenues construction skeleton good functional group compatibility under environmentally benign condition. Based on control experiments cyclic voltammetry data, we suggested plausible reaction mechanism which included anodic oxidation, homolysis iodide, radical addition, 5 ‐ exo dig cyclization, coupling or nucleophilic attack iodide ions cascade.

Язык: Английский

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Gold self-relay catalysis enabling annulative oxygenation of propargylic alcohols with O-nucleophiles

Chemical Communications, Год журнала: 2023, Номер 59(27), С. 4032 - 4035

Опубликована: Янв. 1, 2023

A new gold(I) self-relay catalysis reaction enabling the annulative oxygenation of propargylic alcohols with various O-nucleophiles, such as carboxylic acids, and TBHP, is reported, producing a series functionalized benzofurans in moderate to good yields under mild conditions. This protocol benefits from π- σ-Lewis acid capability gold complexes, demonstrating high molecular convergence, broad substrate flexibility, functional group compatibility

Язык: Английский

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Multicomponent Annulative SO₂ Insertion of Heteroatom‐Linked 1,7‐Diynes for Accessing Tricyclic Sulfones

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1693 - 1698

Опубликована: Май 6, 2023

Abstract A metal‐free radical multicomponent bicyclization of heteroatom‐linked 1,7‐diynes with aryl diazonium tetrafluoroborates and DABCO‐bis(sulfurdioxide) (DABSO) is reported, enabling annulative SO 2 insertion access to produce two types skeletally diverse tricyclic sulfones, namely, thieno[3,4‐ c ]quinoline 2,2‐dioxides ]chromene 2,2‐dioxides, moderate good yields by simply tuning the linkers 1,7‐diynes. This protocol demonstrates remarkable compatibility regarding N ‐ O ‐linked different substitution patterns tetrafluoroborates. magnified image

Язык: Английский

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Electrochemical cascade pyrazole annulation and C-H halogenation for the synthesis of 4-halopyrazoles

Green Synthesis and Catalysis, Год журнала: 2023, Номер unknown

Опубликована: Окт. 1, 2023

The synthesis of 4-halo-functionalized pyrazoles by electrochemical cascade reactions between N,N-dimethyl enaminones and proper hydrazine reagents in the presence a halogen source is realized at room temperature. work provides tunable efficient accesses to 4-chloro- 4-bromopyrazoles aqueous THF (tetrahydrofuran) without using any transition metal reagent.

Язык: Английский

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Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3578 - 3584

Опубликована: Июнь 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Язык: Английский

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Visible-Light-Induced Regioselective Cascade Radical Cyclization of α-Bromocarbonyls: Access to Benzazepine Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2238 - 2246

Опубликована: Янв. 31, 2024

Visible-light-induced regioselective cascade radical cyclization of α-bromocarbonyls for the synthesis benzazepine derivatives is described. In presence fac-Ir(ppy)3 (2.0 mol %) as a photocatalyst, 2,6-lutidine base, and dichloromethane solvent, reactions proceed smoothly to afford seven-membered rings in good yields. This protocol features broad substrate scope, excellent functional group tolerance, mild reaction conditions. Preliminary mechanistic studies reveal that generation α-carbon more prone react with 1,1-diphenylethylene tethered acrylamide generate stable heterocycle.

Язык: Английский

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Electrochemical Synthesis of Spirolactones from α-Tetralone Derivatives with Methanol as a C1 Source

Organic Letters, Год журнала: 2024, Номер 26(23), С. 5016 - 5020

Опубликована: Июнь 3, 2024

Spirolactones are widely found in pharmaceuticals and bioactive natural products. However, efficient environmentally friendly approaches to accessing spirolactones still highly desirable. Herein, a novel electrochemical synthesis of from α-tetralone derivatives with methanol as C1 source is described. This reaction exhibits high efficiency good functional group tolerance.

Язык: Английский

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