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, Journal Year: 2022, Volume and Issue: 122(21), P. 16110 - 16293

Published: Sept. 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.

Language: Английский

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Open science discovery of potent noncovalent SARS-CoV-2 main protease inhibitors

Science, Journal Year: 2023, Volume and Issue: 382(6671)

Published: Nov. 9, 2023

We report the results of COVID Moonshot, a fully open-science, crowdsourced, and structure-enabled drug discovery campaign targeting severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) main protease. discovered noncovalent, nonpeptidic inhibitor scaffold with lead-like properties that is differentiated from current protease inhibitors. Our approach leveraged crowdsourcing, machine learning, exascale molecular simulations, high-throughput structural biology chemistry. generated detailed map plasticity SARS-CoV-2 protease, extensive structure-activity relationships for multiple chemotypes, wealth biochemical activity data. All compound designs (>18,000 designs), crystallographic data (>490 ligand-bound x-ray structures), assay (>10,000 measurements), synthesized molecules (>2400 compounds) this were shared rapidly openly, creating rich, open, intellectual property–free knowledge base future anticoronavirus discovery.

Language: Английский

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Synthesis of Sulfilimines Enabled by Copper-Catalyzed S-Arylation of Sulfenamides

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(11), P. 6310 - 6318

Published: March 9, 2023

Herein, an unprecedented synthetic route to sulfilimines via a copper-catalyzed Chan–Lam-type coupling of sulfenamides is presented. A key success in this novel transformation the chemoselective S-arylation S(II) form S(IV) sulfilimines, overriding competitive, and more thermodynamically favored, C–N bond formation that does not require change sulfur oxidation state. Computations reveal selectivity arises from selective transmetallation event where bidentate sulfenamide coordination through oxygen atoms favors pathway. The mild environmentally benign catalytic conditions enable broad functional group compatibility, allowing variety diaryl or alkyl aryl be efficiently prepared. Chan–Lam procedure could also tolerate alkenylboronic acids as partners afford alkenyl class scaffolds cannot directly synthesized conventional imination strategies. benzoyl-protecting groups conveniently removed product, which, turn, readily transformed into several S(VI) derivatives.

Language: Английский

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Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(9), P. 6078 - 6144

Published: April 17, 2024

Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods their functionalization require them to first be converted into a more activated derivative, while recent years have seen vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can used toward this goal. These broadly classified three categories. Deoxygenative functionalizations, representing derivatization C–O bond, enable alcohol act as leaving group formation new C–C bonds. Etherifications, characterized by O–H represent classical reactivity has been modernized include mild reaction conditions, diverse partners, high selectivities. Lastly, chain reactions described, wherein acts mediator formal C–H alkyl backbone. Each these classes transformation will discussed context intermolecular arylation, alkylation, related reactions, illustrating alcohols harnessed

Language: Английский

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Copper catalysed construction of C-P bond: C-H functionalization

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123512 - 123512

Published: Jan. 1, 2025

Language: Английский

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The emergence of the C–H functionalization strategy in medicinal chemistry and drug discovery

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(83), P. 10842 - 10866

Published: Jan. 1, 2021

Owing to the market competitiveness and urgent societal need, an optimum speed of drug discovery is important criterion for successful implementation. Despite rapid ascent artificial intelligence computational bioanalytical techniques accelerate in big pharma, organic synthesis privileged scaffolds predicted silico vitro vivo studies still considered as rate-limiting step. C-H activation latest technology added into chemist's toolbox construction late-stage modification functional molecules achieve desired chemical physical properties. Particularly, elimination prefunctionalization steps, exceptional group tolerance, complexity-to-diversity oriented synthesis, functionalization medicinal expand space. It has immense potential a library molecules, structural required pharmacological properties such absorption, distribution, metabolism, excretion, toxicology (ADMET) attachment reporters proteome profiling, metabolite etc. preclinical studies. Although heterocycle modification, 18F labelling, methylation, via have been reviewed from synthetic standpoint, general overview these protocols aspects not reviewed. In this feature article, we will discuss recent trends methodologies through activation/annulation cascade; arylation sp2-sp2 sp2-sp3 cross-coupling; borylation/silylation introduce linchpin further manipulation; amination N-heterocycles hydrogen bond acceptors; fluorination/fluoroalkylation tune polarity lipophilicity; methylation: methyl magic discovery; peptide macrocyclization therapeutics biologics; fluorescent labelling radiolabelling bioimaging; bioconjugation biology studies; drug-metabolite biodistribution excretion diversification drug-molecules increase efficacy safety; cutting-edge DNA encoded improved chemistry discovery.

Language: Английский

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Copper anchored on phosphorus g-C₃N₄ as a highly efficient photocatalyst for the synthesis of N-arylpyridin-2-amines

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(2), P. 1041 - 1049

Published: Jan. 1, 2021

A copper modified phosphorus doped g-C₃N₄ (Cu/P-CN) has been prepared and identified as an efficient catalyst for the synthesis of N-arylpyridin-2-amine derivatives by reaction 2-aminopyridine aryl boronic acid under irradiation blue light.

Language: Английский

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Photocatalysis in Dual Catalysis Systems for Carbon‐Nitrogen Bond Formation

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(4), P. 937 - 979

Published: Dec. 25, 2020

Abstract The development of versatile methods for the formation carbon‐nitrogen bonds has significant impact on synthetic chemistry community. However, it remains challenging owing to utilization costly catalyst systems and harsh reaction conditions. Compared conventional methods, photoredox catalysis which harnesses energy from light emerged as an environmentally benign cost‐effective strategy promoting C−N bond constructions. Furthermore, synergistic action with another catalytic process a profound reactivity profiles many traditional routes. Over recent years, immense progress been made towards expediting photocatalysis in dual‐catalysis achieving various industrially important processes under milder This review highlights advancement state‐of‐the‐art achieved these dual‐catalytic platforms construction over last decade. magnified image

Language: Английский

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Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(62), P. 15277 - 15326

Published: Sept. 9, 2021

Abstract This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications title compounds design boron‐containing drugs are surveyed, with special emphasis on α‐amino derivatives. A general overview as modern tools to construct C(sp 3 )−C )‐heteroatom bonds is given, including developments Suzuki‐Miyaura Chan‐Lam cross‐couplings, single‐electron‐transfer processes metallo‐ organocatalytic photoredox reactions, transformations boron “ate” complexes. Finally, an attempt summarize current state art synthesis trifluoroborates made, a brief mention “classical” methods (transmetallation organolithium/magnesium reagents species, anti‐Markovnikov hydroboration alkenes, modification alkenyl compounds) focus methodologies (boronation alkyl (pseudo)halides, derivatives carboxylic alcohols, primary amines, boronative C−H activation, novel approaches alkene hydroboration, 1,2‐metallate‐type rearrangements).

Language: Английский

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An Integrated Carbon Nitride‐Nickel Photocatalyst for the Amination of Aryl Halides Using Sodium Azide

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(24)

Published: March 25, 2022

The synthesis of primary anilines via sustainable methods remains a challenge in organic synthesis. We report photocatalytic protocol for the selective cross-coupling wide range aryl/heteroaryl halides with sodium azide using photocatalyst powder consisting nickel(II) deposited on mesoporous carbon nitride (Ni-mpg-CN

Language: Английский

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