Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

Chemical Reviews, Год журнала: 2010, Номер 110(2), С. 1147 - 1169

Опубликована: Янв. 15, 2010

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTPalladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsThomas W. Lyons and Melanie S. Sanford*View Author Information Department of Chemistry, University Michigan, 930 North Avenue, Ann Arbor, Michigan 48109* To whom correspondence should be addressed. E-mail: [email protected]Cite this: Chem. Rev. 2010, 110, 2, 1147–1169Publication Date (Web):January 15, 2010Publication History Received8 May 2009Published online15 January 2010Published inissue 10 February 2010https://pubs.acs.org/doi/10.1021/cr900184ehttps://doi.org/10.1021/cr900184ereview-articleACS PublicationsCopyright © 2010 American Chemical SocietyRequest reuse permissionsArticle Views81864Altmetric-Citations5606LEARN 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 to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is 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 Other access optionsGet e-Alertsclose SUBJECTS:Chemical reactions,Functionalization,Halogenation,Palladium,Reagents Get e-Alerts

Язык: Английский

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Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality

Angewandte Chemie International Edition, Год журнала: 2009, Номер 48(28), С. 5094 - 5115

Опубликована: Июнь 25, 2009

Abstract Pick your Pd partners : A number of catalytic systems have been developed for palladium‐catalyzed CH activation/CC bond formation. Recent studies concerning the palladium(II)‐catalyzed coupling bonds with organometallic reagents through a II /Pd 0 cycle are discussed (see scheme), and versatility practicality this new mode catalysis presented. Unaddressed questions potential development in field also addressed. magnified image In past decade, bond‐forming reactions emerged as promising transformations; however, is still at an early stage compared to state art cross‐coupling using aryl alkyl halides. This Review begins brief introduction four extensively investigated modes forming CC from bonds: , IV catalysis. more detailed discussion then directed towards recent cycle. Despite progress made date, improving reaction remains tremendous challenge.

Язык: Английский

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Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization

Chemical Reviews, Год журнала: 2012, Номер 112(11), С. 5879 - 5918

Опубликована: Авг. 31, 2012

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTRuthenium(II)-Catalyzed C–H Bond Activation and FunctionalizationPercia Beatrice Arockiam, Christian Bruneau*, Pierre H. Dixneuf*View Author Information Laboratoire Organométalliques, Matériaux et Catalyse, Institut Sciences Chimiques, UMR 6226 CNRS−Université de Rennes1, Campus Beaulieu, 35042 Rennes, France*E-mail: [email protected]; protected]Cite this: Chem. Rev. 2012, 112, 11, 5879–5918Publication Date (Web):August 31, 2012Publication History Received14 April 2012Published online31 August inissue 14 November 2012https://pubs.acs.org/doi/10.1021/cr300153jhttps://doi.org/10.1021/cr300153jreview-articleACS PublicationsCopyright © 2012 American Chemical SocietyRequest reuse permissionsArticle Views41440Altmetric-Citations2535LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is 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 Other access optionsGet e-Alertsclose SUBJECTS:Alcohols,Aromatic compounds,Catalysts,Hydrocarbons,Organic reactions Get e-Alerts

Язык: Английский

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Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Chemical Reviews, Год журнала: 2016, Номер 116(19), С. 12564 - 12649

Опубликована: Сен. 30, 2016

Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption these has been continued development reliable versatile catalysts function under operationally simple, user-friendly conditions. This review provides overview N-arylation found both basic applied research from 2008 present. Selected examples between nine classes nitrogen-based coupling partners (pseudo)aryl halides are described for synthesis heterocycles, medicinally relevant compounds, natural products, organic materials, catalysts.

Язык: Английский

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The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates

Journal of Medicinal Chemistry, Год журнала: 2011, Номер 54(10), С. 3451 - 3479

Опубликована: Апрель 19, 2011

ADVERTISEMENT RETURN TO ISSUEPerspectiveNEXTThe Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit Drug CandidatesStephen D. Roughley*‡ and Allan M. Jordan§View Author Information‡ Vernalis (R&D) Ltd., Granta Park, Cambridge, CB21 6GB, U.K.§ Cancer Research UK Discovery Unit, Paterson Institute for Research, University Manchester, Wilmslow Road, M20 4BX, U.K.*Phone: (+44) 01223 895555. Fax: 895556. E-mail: [email protected]Cite this: J. Med. Chem. 2011, 54, 10, 3451–3479Publication Date (Web):April 19, 2011Publication History Received18 February 2011Published online2 May inissue 26 2011https://pubs.acs.org/doi/10.1021/jm200187yhttps://doi.org/10.1021/jm200187yreview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views51874Altmetric-Citations2000LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is 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 given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting SUBJECTS:Alkyls,Amides,Amines,Aromatic compounds,Chemical reactions Get e-Alerts

Язык: Английский

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Catalysis for fluorination and trifluoromethylation

Nature, Год журнала: 2011, Номер 473(7348), С. 470 - 477

Опубликована: Май 1, 2011

Язык: Английский

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Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications

Chemical Reviews, Год журнала: 2017, Номер 117(13), С. 9247 - 9301

Опубликована: Янв. 4, 2017

Catalytic transformation of ubiquitous C-H bonds into valuable C-N offers an efficient synthetic approach to construct N-functionalized molecules. Over the last few decades, transition metal catalysis has been repeatedly proven be a powerful tool for direct conversion cheap hydrocarbons synthetically versatile amino-containing compounds. This Review comprehensively highlights recent advances in intra- and intermolecular amination reactions utilizing late metal-based catalysts. Initial discovery, mechanistic study, additional applications were categorized on basis scaffolds types reactions. Reactivity selectivity novel systems are discussed three sections, with each being defined by proposed working mode.

Язык: Английский

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Palladium-Catalyzed Transformations of Alkyl C–H Bonds

Chemical Reviews, Год журнала: 2016, Номер 117(13), С. 8754 - 8786

Опубликована: Дек. 2, 2016

This Review summarizes the advancements in Pd-catalyzed C(sp3)-H activation via various redox manifolds, including Pd(0)/Pd(II), Pd(II)/Pd(IV), and Pd(II)/Pd(0). While few examples have been reported of alkane C-H bonds, many activation/C-C C-heteroatom bond forming reactions developed by use directing group strategies to control regioselectivity build structural patterns for synthetic chemistry. A number mono- bidentate ligands also proven be effective accelerating directed weakly coordinating auxiliaries, which provides great opportunities reactivity selectivity (including enantioselectivity) functionalization reactions.

Язык: Английский

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How to Conceptualize Catalytic Cycles? The Energetic Span Model

Accounts of Chemical Research, Год журнала: 2010, Номер 44(2), С. 101 - 110

Опубликована: Ноя. 10, 2010

A computational study of a catalytic cycle generates state energies (the E-representation), whereas experiments lead to rate constants k-representation). Based on transition theory (TST), these are equivalent representations. Nevertheless, until recently, there has been no simple way calculate the efficiency cycle, that is, its turnover frequency (TOF), from theoretically obtained energy profile. In this Account, we introduce energetic span model enables one evaluate TOFs in straightforward manner and affinity with Curtin-Hammett principle. As shown herein, implies change our kinetic concepts. Analogous Ohm's law, chemical current TOF) can be defined by potential (independent mechanism) divided resistance (dependent mechanism nature catalyst). This formulation is based Eyring's TST corresponds steady-state regime. many cycles, only intermediate determine TOF. We call them TOF-determining (TDTS) (TDI). These key states located, among available assessing degree TOF control (X(TOF)); last term resembles structure-reactivity coefficient classical physical organic chemistry. The TDTS-TDI difference reaction driving force define (δE) cycle. Whenever TDTS appears after TDI, δE between two states; when opposite true, must also add difference. Having δE, expressed simply Arrhenius-Eyring fashion, wherein serves as apparent activation An important lesson neither nor step possess all information determines catalyst. Additionally, TDI not necessarily highest lowest states, do they have adjoined single step. such, conclude conceptualization cycles order: catalysis, rate-determining steps, but rather states. include effect reactant product concentrations. approximation, reactants or products located accelerate inhibit reaction. manner, creates direct link experimental quantities theoretical results. versatility demonstrated several organometallic reactions.

Язык: Английский

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Transition metal-catalyzed C–H activation reactions: diastereoselectivity and enantioselectivity

Chemical Society Reviews, Год журнала: 2009, Номер 38(11), С. 3242 - 3242

Опубликована: Янв. 1, 2009

This critical review discusses historical and contemporary research in the field of transition metal-catalyzed carbon–hydrogen (C–H) bond activation through lens stereoselectivity. Research concerning both diastereoselectivity enantioselectivity C–H processes is examined, application concepts this area for development novel carbon–carbon carbon–heteroatom bond-forming reactions described. Throughout review, an emphasis placed on that are (or may soon become) relevant realm organic synthesis (221 references).

Язык: Английский

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