Regioselective electrochemical cascade C–H sulfonylation–bromination of indolizines to access difunctionalized indolizines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2306 - 2312

Published: Jan. 1, 2024

Regioselective electrochemical C–H sulfonylation–bromination between indolizines, sodium sulfinates, and KBr has been established in an undivided cell, which serves as both the brominating agent electrolyte.

Language: Английский

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Electrochemical phosphorothiolation and 1,4-S → C phospho-Fries rearrangement: controlled access to phosphorothiolated and mercapto-phosphono substituted indolizines

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5198 - 5204

Published: Jan. 1, 2023

An unprecedented electrochemically regioselective C–H phosphorothiolation and S- to C-[1,4] phosphonyl migration involving indolizines, elemental sulfur, H-phosphonates in an undivided cell has been developed.

Language: Английский

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Controlled and Site-Selective C–H/N–H Alkenylation, Dialkenylation, and Dehydrogenative β-Alkenylation of Various N-Heterocycles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4840 - 4850

Published: March 19, 2024

Here, we report controlled and site-selective C–H alkenylation dialkenylation of indolizines pyrrolo[1,2-a]quinolines with β-alkoxyvinyl trifluoromethylketones under simple practical conditions. Moreover, this direct strategy can also be extended to imidazo[1,2-a]pyridines. Notably, without a transition metal external oxidant, efficient dehydrogenative β-alkenylation tertiary amines is presented.

Language: Английский

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Transition metal- and oxidant-free [3 + 2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(9), P. 2529 - 2533

Published: Jan. 1, 2022

A transition metal- and oxidant-free C–C/C–N annulation of azomethine imines with vinylene carbonate as dual synthons under simple reaction conditions is described herein.

Language: Английский

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Transition metal-free annulative vinylene transfer via the 1,3-dipolar reaction of N-ylides: access to benzo-fused indolizines

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(48), P. 9604 - 9608

Published: Jan. 1, 2022

An efficient metal-free annulative vinylene transfer protocol for the synthesis of benzo-fused indolizines via 1,3-dipolar cycloadditions N-ylides with carbonate has been developed. Vinylene serves as an acetylene surrogate without any external oxidant involved. This transformation leads to direct construction versatile indolizine derivatives in moderate good yields.

Language: Английский

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Indolizine: A Promising Framework for Developing a Diverse Array of C−H Functionalized Hybrids

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(1)

Published: Jan. 8, 2023

Abstract C−H functionalized indolizines have emerged as a modern sustainable protocol, it offers robust applications in the field of agriculture, medicine and pharmaceutical sciences. In recent times, number effective methods for C−C, C−P C−S bond formation via functionalization been established. The present review article provides thorough assessment developments indolizines. has categorized based on using conventional well non‐conventional methodologies. Moreover, reaction mechanism discussed elaborated form.

Language: Английский

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Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7199 - 7207

Published: May 12, 2023

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium diazo compounds without any additives access library trifunctionalized indolizines in good yields. Besides, isoquinolinium imidazolium also applied this reaction. Of particular note is that various functional groups such -CO2R, -CO2NR2, -CF3, -CN, -(O)P(OR)2 could be easily introduced into cycloaddition products by strategy.

Language: Английский

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Controllable Construction of Vinyl Sulfones and β‐Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(12), P. 1367 - 1372

Published: Feb. 23, 2024

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions. electrochemical C—H proceeded smoothly to afford ( E )‐vinyl sulfones good selectivity in an undivided cell without external oxidant. While aerobic trifunctionalization occurred presence KI air, which provides β ‐keto selenosulfones via formation C—O, C—S, and C—Se bonds one‐pot. Following control experiments, a plausible mechanism is proposed rationalize experimental results.

Language: Английский

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Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: Feb. 29, 2024

Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes

Language: Английский

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Synthesis and Optical Properties of Polyaryl 2‐(Pyridin‐2‐yl)phenol‐Based Four‐Coordinate Organoboron Complexes

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(8), P. 924 - 930

Published: Jan. 10, 2023

Comprehensive Summary A family of polyaryl 2‐(pyridin‐2‐yl)phenol‐based four‐coordinate organoboron complexes were prepared in good yields via deconstructive cycloaromatization indolizines, cyclopropenones, and boric acids. The photoluminescence measurements have revealed that these N,O π ‐ conjugated tetracoordinate boron display bright fluorescence, large Stokes shifts, quantum ( Φ lum = 0.15—0.45). In addition, the DFT calculations carried out to deepen understanding electronic structures optoelectronic properties structurally unprecedented complexes.

Language: Английский

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