Recent Advances in Acyl Suzuki Cross-Coupling

Catalysts, Journal Year: 2019, Volume and Issue: 9(1), P. 53 - 53

Published: Jan. 8, 2019

Acyl Suzuki cross-coupling involves the coupling of an organoboron reagent with acyl electrophile (acyl halide, anhydride, ester, amide). This review provides a timely overview very important advances that have recently taken place in acylative cross-coupling. Particular emphasis is directed toward type electrophiles, catalyst systems and new partners. will be value to synthetic chemists involved this rapidly developing field as well those interested using for synthesis ketones catalytic alternative stoichiometric nucleophilic additions or Friedel-Crafts reactions.

Language: Английский

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Activation of C–O and C–N Bonds Using Non-Precious-Metal Catalysis

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(20), P. 12109 - 12126

Published: Sept. 10, 2020

ADVERTISEMENT RETURN TO ISSUEPREVViewpointNEXTActivation of C–O and C–N Bonds Using Non-Precious-Metal CatalysisTimothy B. BoitTimothy BoitDepartment Chemistry Biochemistry, University California, Los Angeles, California 90095, United StatesMore by Timothy Boit, Ana S. BulgerAna BulgerDepartment Bulger, Jacob E. DanderJacob DanderDepartment Dander, Neil K. Garg*Neil GargDepartment States*E-mail: [email protected]More Garghttp://orcid.org/0000-0002-7793-2629Cite this: ACS Catal. 2020, 10, 20, 12109–12126Publication Date (Web):September 2020Publication History Received30 July 2020Published online10 September inissue 16 October 2020https://pubs.acs.org/doi/10.1021/acscatal.0c03334https://doi.org/10.1021/acscatal.0c03334article-commentaryACS PublicationsCopyright © 2020 American Chemical Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views15643Altmetric-Citations116LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (3 MB) Get e-AlertscloseSUBJECTS:Alkyls,Amides,Coupling reactions,Cross coupling reaction,Organic compounds e-Alerts

Language: Английский

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Acyclic Twisted Amides

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(20), P. 12746 - 12783

Published: Aug. 18, 2021

In this contribution, we provide a comprehensive overview of acyclic twisted amides, covering the literature since 1993 (the year first recognized report on amides) through June 2020. The review focuses classes amides and their key structural properties, such as amide bond twist nitrogen pyramidalization, which are primarily responsible for disrupting

Language: Английский

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Contemporary Approaches for Amide Bond Formation

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4359 - 4391

Published: Nov. 7, 2023

Abstract Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out thirty‐seven new drugs approved by FDA 2022, eleven are small molecules containing at least amide bond. Additionally, there nineteen large as drugs, some which have peptide structures, and therefore, also bear bonds. In years, multiple teams embraced challenge developing more efficient methods for formation. This dedication led numerous publications appearing monthly prestigious journals, showcasing advancements this field. The primary goal review is present viable strategies constructing It crucial differentiate between formation synthesis; hence, focus on describing specific forming C(O)−N particular, concentrates developed within last six years. There a particular emphasis approaches that consider thought process when selecting starting materials groups. approach ensures coverage all common chemical transformations yield

Language: Английский

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Atomic-Scale Tailoring C–N Coupling Sites for Efficient Acetamide Electrosynthesis over Cu-Anchored Boron Nitride Nanosheets

ACS Nano, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Electrochemical conversion of carbon and nitrogen sources into valuable chemicals provides a promising strategy for mitigating CO

Language: Английский

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Catalytic Reductive Functionalization of Tertiary Amides using Vaska’s Complex: Synthesis of Complex Tertiary Amine Building Blocks and Natural Products

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(15), P. 8880 - 8897

Published: July 27, 2020

The tertiary amide is a ubiquitous functional group and plays an irreplaceable role in medicinal chemistry. Its robust nature has meant—in the past—that selective manipulation of this motif remained elusive. reductive activation through hydrosilylation amides—using Vaska's complex (IrCl(CO)(PPh3)2)—has emerged as powerful strategy for chemoselective transformation amides into reactive enamines iminium ions. Furthermore, these synthetically valuable species can be accessed presence traditionally more groups. This approach to via been exploited range downstream C–C bond forming processes seen significant applications total synthesis, enabling streamlined routes synthesis natural product architectures. perspective covers development synthetic strategy, from initial studies its flourishing use functionalization amide-containing molecules, both simple complex.

Language: Английский

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Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(46), P. 18437 - 18443

Published: Nov. 12, 2019

Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, generation new C–X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering amides electrophilic through mild and chemoselective umpolung transformation, broad range widely available oxygen, nitrogen, sulfur, halogen nucleophiles can be used to generate α-functionalized amides. More 60 examples are presented establish generality this process, calculations mechanistic aspects underline fragmentation pathway that accounts for broadness methodology.

Language: Английский

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Direct Synthesis of Enamides via Electrophilic Activation of Amides

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(28), P. 10524 - 10529

Published: July 7, 2021

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination LiHMDS and triflic anhydride, which serves as both electrophilic activator oxidant, characterized by its simple setup broad substrate scope. The synthetic utility formed was readily demonstrated in a range downstream transformations.

Language: Английский

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Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(16), P. 8827 - 8831

Published: Jan. 23, 2021

The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation phosphonylation secondary amides have been accomplished for the first time synthesis enantioenriched α-aminonitriles α-aminophosphonates. protocol is highly efficient enantioselective, providing a novel route optically active α-functionalized amines from simple, readily available feedstocks. In addition, reactions are scalable catalyst can be recycled reused.

Language: Английский

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Three‐Component Aminoarylation of Electron‐Rich Alkenes by Merging Photoredox with Nickel Catalysis

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(26), P. 14399 - 14404

Published: April 19, 2021

A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and thioethers by synergistic photoredox nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition the to alkene Ni-mediated radical/transition metal cross over lead corresponding product. The cascade, which can be conducted under practical mild conditions, features high functional group tolerance broad substrate scope. Stereoselective achieved using a L-(+)-lactic acid derived ether substrate, offering novel route for preparation enantiopure α-arylated β-amino alcohols. In addition, 1,2-aminoacylation ethers an acyl succinimide electrophile coupling.

Language: Английский

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