Sonochemistry and Copper Catalysis: An Efficient Duo in the Synthesis of Chalcogenylindolizines DOI
Filipe Penteado, Luana Bettanin,

Kethelyn Machado

et al.

Asian Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 9(10), P. 1631 - 1637

Published: July 13, 2020

Abstract Herein, we describe an efficient and selective Cu‐catalyzed C−H bond chalcogenation of the indolizine core, in presence DMSO applying ultrasound irradiation as alternative energy source. Under optimal conditions, 3‐sulfanylindolizines (16 examples) were prepared moderate to good yields starting from diorganyl disulfides 2‐arylindolizines. When diphenyl diselenide was used, 1,3‐bis(selanyl) indolizines (4 exclusively obtained very yields. The use makes reaction faster more when compared conventional heating.

Language: Английский

Chelation-assisted transition metal-catalysed C–H chalcogenylations DOI Open Access
Wenbo Ma, Nikolaos Kaplaneris,

Xinyue Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(8), P. 1022 - 1060

Published: Jan. 1, 2020

This review summarizes recent advances in C–S and C–Se formationsviatransition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selectivity.

Language: Английский

Citations

80

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light DOI Creative Commons
Ignacio D. Lemir, Willber D. Castro‐Godoy, Adrián A. Heredia

et al.

RSC Advances, Journal Year: 2019, Volume and Issue: 9(39), P. 22685 - 22694

Published: Jan. 1, 2019

A novel and sustainable procedure was developed for the synthesis of 3-selenylindoles employing diorganyl diselenides indoles or electron-rich arenes as starting materials. Visible blue light used to promote reaction without transition metal complexes organic photocatalysts sensitizers. Additives such strong oxidants bases were not required. Moreover, ethanol employed a benign solvent under mild conditions. Through this easy eco-friendly approach, several number asymmetric diarylselenides obtained in good excellent isolated yields.

Language: Английский

Citations

56

Photocatalytic Synthesis of 3‐Sulfanyl‐ and 1,3‐Bis(sulfanyl)indolizines Mediated by Visible Light DOI
Filipe Penteado, Caroline Signorini Gomes,

Loana I. Monzon

et al.

European Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 2020(14), P. 2110 - 2115

Published: March 17, 2020

A metal‐free method for the synthesis of 3‐sulfanyl indolizines from thiols and 2‐arylindolizines, is reported. The reaction mediated by eosin Y under blue LED light irradiation uses atmospheric oxygen as oxidant. By use a catalytic amount I 2 , corresponding 1,3‐bis‐sulfanyl are obtained, in good yields.

Language: Английский

Citations

33

Electrochemical site-selective direct C–H sulfenylation and selenylation of a chromone-fused-indolizine (CFI) skeleton DOI

Pooja Kumari Jat,

Lalit Yadav,

Amreen Chouhan

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(36), P. 5415 - 5418

Published: Jan. 1, 2023

For the first time, we report transition metal-free electrochemical site-selective direct C–H sulfenylation/selenylation of chromone-fused indolizine compounds (CFIs) to afford corresponding CFIs thioethers and selenoethers in 58–96% yields.

Language: Английский

Citations

10

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis DOI
Reetu Reetu,

Sangita Kalita,

Sonali Prava Dash

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 17, 2024

Abstract Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis use iodine DMSO in various synthetic routes for preparation valuable targets presented. These reduce acceptance on expensive additives reagents, offer more sustainable solution these scaffolds.

Language: Английский

Citations

3

N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides DOI Open Access

Dengpeng Xia,

Jinyun Luo,

Lin He

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(2), P. 622 - 622

Published: Jan. 1, 2024

An efficient method for the construction of C(sp 2 )-S bond has been developed.The stable N-heterocyclic carbene 1,3-bis(2,6-dissopropylphenyl)-imidazole-2-ylidene can activate C -Si pentafluorophenyl trimethylsilicon effectively to initiate nucleophilic substitution reaction with thiosulfonic ester, producing sulfide products in 34%~98% yields.Keywords carbene; C-S bond; 碳-硫(C-S)键广泛存在于天然产物、生物活性化 合物、药物以及功能材料中, 因此 键的构建一直 是有机合成领域中的研究热点 [1] .在过去几十年中, 过 渡金属催化的交叉偶联反应、插入反应、硫代羰基化、 亲核加成反应等已经被广泛地用于 键的构建 [2] .另外, 多氟芳烃很多为重要的结构单元, 广泛存在于药 物分子和聚合物中, 因此合成五氟芳基硫醚化合物在有 机化学中具有重要意义 [3] .在过去的几十年里, 化学家 发展了几种合成五氟苯基硫醚化合物的方法.Kita 课题 组 [4] 在 2001 年通过 TMSOTf 催化富电子芳烃与醌单-O,S-缩醛的亚磺酰化和亲核加成反应获得了五氟苯基 硫醚化合物, 但该反应需要在低温条件下进行(Scheme 1a).Shi 课题组 [5] 用 Cu(I)催化五氟苯与二芳基二硫醚发 生交叉偶联反应(Scheme 1b), 得到相应的五氟苯基硫 醚, Peng [6] Ni(0)催化硫醇和芳基碘化物分子间 交叉偶联反应快速地合成了多种五氟苯基硫醚(Scheme Sakai [7] Pd(II)/Cu(II)催化二芳基二硫醚与 芳烃的交叉偶联反应(Scheme 得到五氟苯基硫醚 化合物.此外, Shibata [8] 通过活化的 α-亚甲基酮、 环状 1,3-二酮、 内酰胺和内酯与 6 F 5 -DAST 的脱酰基五 氟苯基硫化反应(Scheme 得到五氟苯基环硫醚衍 生物.然而这些方法一般都需要过渡金属催化剂催化, 有的还需要高温等较为苛刻的反应条件.我们课题组 [9] 前期利用膦腈碱 t-Bu-P 4 作为强有机 Lewis 碱催化剂, 实 现了有机小分子催化下五氟苯基硅试剂与硫代磺酸酯 的亲核取代反应(Scheme 1c), 制备了多种五氟苯基硫醚 化合物, 但膦腈碱催化剂价格非常昂贵, 在实验室制备 困难, 且该催化剂对水和空气高度敏感, 实验操作需要 极其严苛的无水无氧条件.因此, 该方法的实际应用受 到了一定的限制.

Language: Английский

Citations

3

Iron-Catalyzed Thioarylation of Arenes Using Saccharin-Derived Reagents DOI Creative Commons
Lachlan J. N. Waddell, Oluwajuwon A. M. Okunade,

Amy C. Dodds

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 16, 2025

Biaryl sulfides are important scaffolds found in various natural products and pharmaceutically active compounds. One of the main approaches for synthesis this compound class involves substitution arenes using electrophilic thioaryl species. However, these methods generally require acidic activation electrophile, more forcing conditions, long reaction times. Here, we describe combination super Lewis acid iron(III) triflimide with saccharin-based thioarylation reagents rapid unsymmetrical biaryl under mild conditions. This approach was effective electron-deficient species that performed poorly previous methods, allowing efficient functionalization bioactive

Language: Английский

Citations

0

A review on the latest progress of C‐S cross‐coupling in diaryl sulfide synthesis: Update from 2012 to 2021 DOI
Fahimeh Abedinifar, Saeed Bahadorikhalili, Bagher Larijani

et al.

Applied Organometallic Chemistry, Journal Year: 2021, Volume and Issue: 36(1)

Published: Oct. 14, 2021

Diaryl sulfides are a highly valuable class of sulfur‐containing compounds presented in numerous drugs with broad range therapeutic activities and also employed as precursors to other higher oxidation state important bioactivities. Thus, the development efficient approaches for C−S bond formation is essential synthetic medicinal chemistry. Many efforts have been made constructing bonds via various protocols. This review highlights current strategies emphasizing metal‐catalyzed reactions (MRC), metal‐free approaches, photocatalysis reaction s , MCR's from 2012 onwards.

Language: Английский

Citations

23

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds DOI
Chang‐Sheng Wang, Yuan Xu, Shaopeng Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(4), P. 645 - 681

Published: Dec. 23, 2023

Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- atom-economical method for the synthesis chalcogen-bearing compounds. Nevertheless, direct severely lags behind C-C, C-N C-O bond formations. Moreover, compared with monochalcogenation, reports selective mono-/dichalcogenation exclusive dichalcogenation relatively scarce. The past decade witnessed significant advancements various C(sp

Language: Английский

Citations

9

Regioselective C–H dithiocarbamation of indolizines with tetraalkylthiuram disulfide under metal-free conditions DOI
Xiang Liu, Dan Song, Zemin Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(24), P. 5284 - 5288

Published: Jan. 1, 2021

An efficient and straightforward metal-free regioselective C–H dithiocarbamation of indolizines with tetraalkylthiuram disulfide has been described. A series indolizines-dithiocarbamates derivatives were easily accessed in good yields.

Language: Английский

Citations

19