CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

Angewandte Chemie International Edition, Год журнала: 2012, Номер 51(36), С. 8960 - 9009

Опубликована: Авг. 6, 2012

Abstract The direct functionalization of CH bonds in organic compounds has recently emerged as a powerful and ideal method for the formation carbon–carbon carbon–heteroatom bonds. This Review provides an overview bond strategies rapid synthesis biologically active such natural products pharmaceutical targets.

Язык: Английский

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Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups

Organic Chemistry Frontiers, Год журнала: 2015, Номер 2(9), С. 1107 - 1295

Опубликована: Янв. 1, 2015

In this review, a summary of transition metal-catalyzed C–H activation by utilizing the functionalities as directing groups is presented.

Язык: Английский

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Copper‐Catalyzed Aerobic Oxidative CH Functionalizations: Trends and Mechanistic Insights

Angewandte Chemie International Edition, Год журнала: 2011, Номер 50(47), С. 11062 - 11087

Опубликована: Окт. 27, 2011

The selective oxidation of C-H bonds and the use O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is versatile oxidant, capable promoting wide range oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich molecules. Many these can be rendered catalytic Cu employing molecular oxygen to regenerate active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed feature substrates that are electron-deficient or appear unlikely undergo copper(II). In some cases, evidence has been obtained for involvement organocopper(III) intermediates reaction mechanism. Organometallic this type important new opportunities field aerobic oxidations.

Язык: Английский

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Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds

Accounts of Chemical Research, Год журнала: 2015, Номер 48(4), С. 1053 - 1064

Опубликована: Март 10, 2015

ConspectusIn recent years, carbon–hydrogen bond functionalization has evolved from an organometallic curiosity to a tool used in mainstream applications the synthesis of complex natural products and drugs. The use C–H bonds as transformable functional group is advantageous because these are most abundant functionality organic molecules. One-step conversion desired shortens synthetic pathways, saving reagents, solvents, labor. Less chemical waste generated well, showing that this chemistry environmentally beneficial. This Account describes development bidentate, monoanionic auxiliaries for transition-metal-catalyzed reactions. was initially developed overcome limitations with palladium-catalyzed assisted by monodentate directing groups. By electron-rich bidentate groups, unactivated sp3 under palladium catalysis been developed. Furthermore, number base-metal complexes catalyze sp2 bonds. At point, aminoquinoline, picolinic acid, related compounds among versatile moieties chemistry. These groups facilitate catalytic iron, cobalt, nickel, copper, ruthenium, rhodium, complexes. Exceptionally general reactivity observed, enabling, other transformations, direct arylation, alkylation, fluorination, sulfenylation, amination, etherification, carbonylation, alkenylation versatility auxilaries can be attributed following factors. First, they capable stabilizing high oxidation states transition metals, thereby facilitating step. Second, removed, enabling their medicinally relevant substances. While presents significant advance, several methodology apparent. expensive second-row metal catalysts still required efficient functionalization. need install subsequently remove relatively disadvantage.

Язык: Английский

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Radicals: Reactive Intermediates with Translational Potential

Journal of the American Chemical Society, Год журнала: 2016, Номер 138(39), С. 12692 - 12714

Опубликована: Сен. 15, 2016

This Perspective illustrates the defining characteristics of free radical chemistry, beginning with its rich and storied history. Studies from our laboratory are discussed along recent developments emanating others in this burgeoning area. The practicality chemoselectivity reactions enable rapid access to molecules relevance drug discovery, agrochemistry, material science, other disciplines. Thus, these reactive intermediates possess inherent translational potential, as they can be widely used expedite scientific endeavors for betterment humankind.

Язык: Английский

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Iron-Catalyzed C–H Bond Activation

Chemical Reviews, Год журнала: 2017, Номер 117(13), С. 9086 - 9139

Опубликована: Апрель 5, 2017

Catalytic C-H bond activation, which was an elusive subject of chemical research until the 1990s, has now become a standard synthetic method for formation new C-C and C-heteroatom bonds. The potential activation first described ruthenium catalysis is widely exploited by use various precious metals. Driven increasing interest in utilization ubiquitous metals that are abundant nontoxic, iron rapidly growing area research, iron-catalyzed been most actively explored recent years. In this review, we summarize development stoichiometric long history, catalytic functionalization, emerged about 10 years ago. We focus review on reactions take place via reactive organoiron intermediates, excluded those as Lewis acid or radical initiator. contents categorized type cleaved formed thereafter, it covers simple substrates possessing directing group anchors catalyst to substrate, providing overview iron-mediated reported literature October 2016.

Язык: Английский

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Funktionalisierung von C‐H‐Bindungen: neue Synthesemethoden für Naturstoffe und Pharmazeutika

Angewandte Chemie, Год журнала: 2012, Номер 124(36), С. 9092 - 9142

Опубликована: Авг. 7, 2012

Abstract Die direkte Funktionalisierung von C‐H‐Bindungen in organischen Molekülen hat sich jüngster Zeit zu einer wirksamen und idealen Methode entwickelt, mit der Kohlenstoff‐Kohlenstoff‐ Kohlenstoff‐Heteroatom‐Bindungen geknüpft werden können. Der Aufsatz gibt einen Überblick über die Strategien, durch eine rasche Synthese biologisch aktiven Verbindungen wie Naturstoffen pharmazeutischen Zielsubstanzen ermöglichen.

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From C(sp2)–H to C(sp3)–H: systematic studies on transition metal-catalyzed oxidative C–C formation

Chemical Society Reviews, Год журнала: 2012, Номер 41(17), С. 5588 - 5588

Опубликована: Янв. 1, 2012

In this tutorial review, we will summarize our recent efforts in transition metal-catalyzed oxidative coupling via C-H functionalization of aromatic, benzylic and allylic bonds. Related works from other laboratories be cited where suitable, aiming to give the readers a flavor field. Special emphasis is placed on reaction design development.

Язык: Английский

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Transition-Metal-Catalyzed Direct Addition of Unactivated C–H Bonds to Polar Unsaturated Bonds

Chemical Reviews, Год журнала: 2015, Номер 115(9), С. 3468 - 3517

Опубликована: Март 9, 2015

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTTransition-Metal-Catalyzed Direct Addition of Unactivated C–H Bonds to Polar Unsaturated BondsLei Yang and Hanmin Huang*View Author Information State Key Laboratory for Oxo Synthesis Selective Oxidation, Lanzhou Institute Chemical Physics, Chinese Academy Sciences, 730000, China*E-mail: [email protected]Cite this: Chem. Rev. 2015, 115, 9, 3468–3517Publication Date (Web):March 2015Publication History Received22 October 2014Published online9 March 2015Published inissue 13 May 2015https://pubs.acs.org/doi/10.1021/cr500610phttps://doi.org/10.1021/cr500610preview-articleACS PublicationsCopyright © 2015 American SocietyRequest reuse permissionsArticle Views16728Altmetric-Citations667LEARN 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 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-Alertsclose SUBJECTS:Addition reactions,Aldehydes,Aromatic compounds,Catalysts,Hydrocarbons Get e-Alerts

Язык: Английский

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Evolution of C–H Bond Functionalization from Methane to Methodology

Journal of the American Chemical Society, Год журнала: 2015, Номер 138(1), С. 2 - 24

Опубликована: Ноя. 13, 2015

This Perspective presents the fundamental principles, elementary reactions, initial catalytic systems, and contemporary catalysts that have converted C–H bond functionalization from a curiosity to reality for synthetic chemists. Many classes of reactions involving transition-metal complexes cleave bonds at typically unreactive positions. These coupled with separate or simultaneous process lead products containing new C–C, C–N, C–O bonds. Such were initially studied conversion light alkanes liquid products, but they been used (and commercialized in some cases) most often synthesis more complex structures natural medicinally active compounds, aromatic materials. change direction research is remarkable because must occur an unactivated over functional groups are reactive than toward classical reagents. The scope form C–C install functionality will be presented, potential future utility these discussed.

Язык: Английский

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