Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Chemical Reviews, Год журнала: 2022, Номер 122(21), С. 16110 - 16293

Опубликована: Сен. 16, 2022

In the present review, we discuss recent progress in field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling and catalytic addition reactions. The development advanced systems is aimed at improved catalyst efficiency, reduced loading, better cost environmental concerns, higher selectivity yields. important rise research efforts sustainability green chemistry areas critically assessed. paramount role mechanistic studies a new generation addressed, key achievements, problems, challenges summarized for this field.

Язык: Английский

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Chiral Transient Directing Groups in Transition-Metal-Catalyzed Enantioselective C–H Bond Functionalization

ACS Catalysis, Год журнала: 2020, Номер 10(21), С. 12898 - 12919

Опубликована: Окт. 21, 2020

Transition-metal-catalyzed C–H bond functionalization has known a rapid evolution in the last years, offering modern strategies for reaching high molecular complexity step- and atom-economical way. Despite indisputable advances, selectivity issues still remain, given ubiquity of bonds on molecules; thus, several approaches have been developed to tackle this challenge. Among them, use transient directing group emerged as an effective tool, circumventing need extra synthetic steps install then cleave molecule. More recently, strategy successfully applied even more challenging transition-metal-catalyzed enantioselective functionalization. This review will highlight discuss main advances made chiral C(sp2)–H C(sp3)–H by transition-metal catalysis.

Язык: Английский

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Transient imine directing groups for the C–H functionalisation of aldehydes, ketones and amines: an update 2018–2020

Organic & Biomolecular Chemistry, Год журнала: 2020, Номер 18(37), С. 7291 - 7315

Опубликована: Янв. 1, 2020

This review describes recent advances in C–H functionalisation using transient directing groups. Advances group design, new bond forming methodologies, regio- and stereoselective processes, mechanistic insights are discussed.

Язык: Английский

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Transient directing ligands for selective metal-catalysed C–H activation

Nature Reviews Chemistry, Год журнала: 2021, Номер 5(9), С. 646 - 659

Опубликована: Июль 20, 2021

Язык: Английский

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Pd^II–Catalyzed Site-selective β- and γ-C(sp³)–H Arylation of Primary Aldehydes Controlled by Transient Directing Groups

Journal of the American Chemical Society, Год журнала: 2022, Номер 144(11), С. 4727 - 4733

Опубликована: Март 14, 2022

Pd(II)-catalyzed site-selective β- and γ-C(sp3)-H arylation of primary aldehydes is developed by rational design L,X-type transient directing groups (TDG). External 2-pyridone ligands are identified to be crucial for the observed reactivity. By minimizing loading acid additives, ligand effect enhanced achieve high reactivities challenging aldehyde substrates. Site selectivity can switched from proximate relatively remote position changing bite angle TDG match desired palladacycle size. Experimental computational investigations support this rationale designing potentially C(sp3)-H functionalizations.

Язык: Английский

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Rh(III)-Catalyzed Atroposelective C–H Selenylation of 1-Aryl Isoquinolines

ACS Catalysis, Год журнала: 2024, Номер 14(8), С. 6009 - 6015

Опубликована: Апрель 5, 2024

Rhodium(III)-catalyzed atroposelective C–H selenylation of 1-aryl isoquinolines has been achieved. The direct reaction between and 2-(phenylselanyl)isoindoline-1,3-dione in the presence chiral SCpRh(III) complex afforded a series axially isoquinoline selenides up to 95% yield 96% ee. features mild conditions broad substrate scope. DFT calculations revealed that C–Se bond formation step proceeds through formal SN2 pathway.

Язык: Английский

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A Chemistry for Incorporation of Selenium into DNA‐Encoded Libraries

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(32), С. 13273 - 13280

Опубликована: Апрель 13, 2020

Abstract Conventional direct C−H selenylation suffers from simple selenation with limited atom economy and complicated reaction system. In this work, we designed benzoselenazolone as a novel bifunctional selenide reagent for both off‐ on‐DNA under rhodium(III) catalysis. We show that using allowed production of series products containing an adjacent aminoacyl group in fast efficient way, high economy. The synthetic application method was demonstrated by taking advantage the amide functionality nucleophile, directing group, coupling partner. This work shows great potential facilitating rapid construction selenium‐containing DNA‐encoded chemical libraries (SeDELs), lays foundation development drugs.

Язык: Английский

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Transient Directing Groups in Metal−Organic Cooperative Catalysis

Chemistry - A European Journal, Год журнала: 2021, Номер 27(56), С. 13899 - 13952

Опубликована: Июль 19, 2021

The direct functionalization of C-H bonds is among the most fundamental chemical transformations in organic synthesis. However, when innate reactivity substrate cannot be utilized for a given single bond, this selective bond mostly relies on use directing groups that allow bringing catalyst close proximity to activated and these need installed before cleaved after transformation, which involves two additional undesired synthetic operations. These steps dramatically reduce overall impact attractiveness techniques since classical approaches based pre-functionalization are sometimes still more straightforward appealing. During past decade, different approach involving both situ installation removal group, can then often used catalytic manner, has emerged: transient group strategy. In addition its innovative character, strategy brought an unprecedented level usefulness enabled development remarkably efficient processes introduction functional onto aromatic aliphatic substrates. unlocked by will comprehensively overviewed review article.

Язык: Английский

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Diorganyl diselenides: a powerful tool for the construction of selenium containing scaffolds

Dalton Transactions, Год журнала: 2021, Номер 50(37), С. 12764 - 12790

Опубликована: Янв. 1, 2021

Organoselenium compounds find versatile applications in organic synthesis, materials and ligand chemistry.

Язык: Английский

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Visible-Light-Mediated Regioselective C3–H Selenylation of Pyrazolo[1,5-a]pyrimidines Using Erythrosine B as Photocatalyst

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8992 - 9003

Опубликована: Июнь 11, 2023

A visible-light-induced efficient methodology has been developed for the C–H selenylation of pyrazolo[1,5-a]pyrimidine derivatives employing erythrosine B as photocatalyst. This is first report on regioselective pyrazolo[1,5-a]pyrimidines. The efficiency this different electron-rich heterocycles like pyrazole, indole, imidazo[1,2-a]pyridine, imidazo[2,1-b]thiazole, and 4-(phenylamino)-2H-chromen-2-one also demonstrated. exploration a photocatalyst with simple mild procedure, wide substrate scope, practical applicability employment eco-friendly energy, oxidant, solvent are attractive characteristics methodology.

Язык: Английский

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