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

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8313 - 8327

Published: Jan. 1, 2023

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

Language: Английский

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Recent Advances in Cyclization Reactions of 1,6‐Enynes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268

Published: Jan. 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.

Language: Английский

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

Molecules, Journal Year: 2023, Volume and Issue: 28(7), P. 3027 - 3027

Published: March 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.

Language: 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, Journal Year: 2024, Volume and Issue: 27(10)

Published: Jan. 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.

Language: Английский

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

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(27), P. 4032 - 4035

Published: Jan. 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

Language: 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, Journal Year: 2024, Volume and Issue: 366(17), P. 3578 - 3584

Published: June 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.

Language: Английский

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Electrochemical Annulation of p-Alkoxy or p-Hydroxy Anilines with Enaminones for Selective Indole and Benzofuran Synthesis

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The green and sustainable electrochemical oxidative cyclization of enaminones with p-methoxy/p-hydroxy anilines has been developed, enabling the regioselective synthesis indoles benzofurans. methods are significant advantage not only due to mild metal-free conditions, but also because employment easily available stable aniline substrates replace unstable quinoneimide for a similar annulation in previous work.

Language: Английский

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

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 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.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 5016 - 5020

Published: June 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.

Language: Английский

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Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Language: Английский

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