Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents DOI Creative Commons

Jinli Nie,

Ziqing He,

Sijie Xie

и другие.

Molecules, Год журнала: 2024, Номер 29(11), С. 2485 - 2485

Опубликована: Май 24, 2024

Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most methods for synthesis alkyl thioethers employ foul-smelling thiols as starting materials or generate them by-products. Additionally, air-sensitive easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method synthesizing is necessary. This paper reports simple, effective, green dialkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K thiol surrogate. transformation offers broad substrate scope good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated nucleophilic substitution halides transition-metal-free base-free conditions.

Язык: Английский

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis DOI Open Access

Juan M. Sonego,

Sheila I. de Diego,

Sergio H. Szajnman

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(52)

Опубликована: Июнь 28, 2023

Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.

Язык: Английский

Процитировано

52

Iodine-dependent oxidative regioselective aminochalcogenation of indolines DOI
Xiaoxiang Zhang, Chenrui Liu, Wanxing Wei

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(9), С. 1152 - 1155

Опубликована: Янв. 1, 2024

An efficient approach for the selective construction of C2,3- or C2,5-aminochalcogenated indole derivatives has been developed, which enables oxidative regioselective aminochalcogenation indolines with amines and dichalconides.

Язык: Английский

Процитировано

7

Iodine-mediated oxidative triple functionalization of indolines with azoles and diazonium salts DOI
Yifeng Liu,

Xiaoting Gu,

Xiaoxiang Zhang

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(34), С. 4613 - 4616

Опубликована: Янв. 1, 2024

We report an innovative synthetic strategy for the generation of polysubstituted indoles from indolines, aryldiazonium salts, and azoles. The methodology encompasses electrophilic substitution reaction affording C5-indoline intermediates which undergo iodine-mediated oxidative transformation coupled with C-H functionalization to yield indole derivatives.

Язык: Английский

Процитировано

6

Catalyst- and additive-free annulation/aromatization leading to benzothiazoles and naphthothiazoles DOI
Zhenhua Xu, Huawen Huang, Hongbiao Chen

и другие.

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(17), С. 3060 - 3064

Опубликована: Янв. 1, 2019

Catalyst- and additive-free three-component annulation/aromatization enable a highly efficient entry to naphtho[1,2-d]thiazoles benzo[d]thiazoles.

Язык: Английский

Процитировано

53

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals DOI
Alexander S. Budnikov, Igor B. Krylov, Olga M. Mulina

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Язык: Английский

Процитировано

14

Ni0/Niδ+ Synergistic Catalysis on a Nanosized Ni Surface for Simultaneous Formation of C–C and C–N Bonds DOI
Jian Zhang, Zhe An, Yanru Zhu

и другие.

ACS Catalysis, Год журнала: 2019, Номер 9(12), С. 11438 - 11446

Опубликована: Ноя. 5, 2019

Simultaneous formation of C–C/C–N bonds provides insight into the bottom-up synthesis N-heterocycles. This work reports Ni0/Niδ+ synergistic catalysis on surface Ni nanoparticles for highly efficient one-pot bonds, affording 1,2,3,4-tetrahydroquinoline and its derivatives from 2-amino benzyl alcohol ethanol without any addition liquor base or external hydrogen. has been achieved by regulating particle size activating with O2. In dehydrogenation −CH2–OH to −CH═O, C══C C═N via concurrent cross-condensation, transformation C═C/C═N hydrogen transfer, found be rate-determining step. Reducing effectively increases number Niδ+ sites, which accelerates catalytic through between Ni0 sites. The sites can further increased appropriately

Язык: Английский

Процитировано

39

Straightforward access to novel indolo[2,3-b]indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles DOI
Taoyuan Liang,

Lingzhen Gong,

He Zhao

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(18), С. 2807 - 2810

Опубликована: Янв. 1, 2020

Unprecedented direct access to novel 2-diarylaminoindolo[2,3-b]indoles via aerobic copper-catalyzed [3+2] annulation of diarylamines and indoles is demonstrated.

Язык: Английский

Процитировано

35

Silver-Catalyzed Remote C5–H Selenylation of Indoles DOI

Song Wei-hong,

Jia Shi, Xiaohong Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(17), С. 11104 - 11115

Опубликована: Июль 29, 2020

Remote C-H functionalization at C5 is the most sparingly observed selectivity in of indole templates. Herein, we reported that combination a AgSbF6 catalyst and phenyliodine diacetate oxidation enabled selenylation position scaffolds selective version, thus leading to formation wide scope 5-selenylated derivatives, which are otherwise difficult prepare. Mechanistic studies indicated current transformation follows radical process, tethered C3 pivaloyl group on plays roles both blocking active manipulating electronic affinity arenes.

Язык: Английский

Процитировано

28

Access to Phenothiazine Derivatives via Iodide-Mediated Oxidative Three-Component Annulation Reaction DOI
Qinghua Chen,

Rong Xie,

Huanhuan Jia

и другие.

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(8), С. 5629 - 5637

Опубликована: Март 23, 2020

Herein, a new iodide-mediated three-component annulation reaction of secondary anilines, cyclohexanones, and elemental sulfur is demonstrated, which allows access to various phenothiazines with the merits formation multiple chemical bonds in one single operation, high step atom efficiency, readily available feedstocks catalyst system, good substrate functional group compatibility. The developed chemistry capable constructing novel structural diversity offers significant basis for further applications.

Язык: Английский

Процитировано

21

Site-specific C–H chalcogenation of quinoxalin-2(1H)-ones enabled by Selectfluor reagent DOI
Jinwei Yuan, Yang Zhang,

Guang-Chao Huang

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(24), С. 6937 - 6949

Опубликована: Янв. 1, 2021

A site-specific C6–H chalcogenation of quinoxalin-2(1 H )-ones with various diselenides and dithiols is presented by employing Selectfluor reagent as an oxidant.

Язык: Английский

Процитировано

16