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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Palladium‐Catalyzed Cross‐Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize

Angewandte Chemie International Edition, Год журнала: 2012, Номер 51(21), С. 5062 - 5085

Опубликована: Май 9, 2012

In 2010, Richard Heck, Ei-ichi Negishi, and Akira Suzuki joined the prestigious circle of Nobel Laureate chemists for their roles in discovering developing highly practical methodologies C-C bond construction. From original contributions early 1970s landscape strategies methods organic synthesis irreversibly changed modern chemist, both academia industry. this Review, we attempt to trace historical origin these powerful reactions, outline developments from seminal discoveries leading eminent position as appreciated applied today.

Язык: Английский

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Catalytic Functionalization of C(sp²)H and C(sp³)H Bonds by Using Bidentate Directing Groups

Angewandte Chemie International Edition, Год журнала: 2013, Номер 52(45), С. 11726 - 11743

Опубликована: Сен. 17, 2013

C-H bonds are ubiquitous in organic compounds. It would, therefore, appear that direct functionalization of substrates by activation would eliminate the multiple steps and limitations associated with preparation functionalized starting materials. Regioselectivity is an important issue because molecules can contain a wide variety bonds. The use directing group largely overcome regiocontrol allowing catalyst to come into proximity targeted A functional groups have been evaluated for as transformation In 2005, Daugulis reported arylation unactivated C(sp(3))-H using 8-aminoquinoline picolinamide bidentate groups, Pd(OAc)2 catalyst. Encouraged these promising results, number transformations since developed systems based on groups. this Review, recent advances area discussed.

Язык: Английский

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The Cross‐Dehydrogenative Coupling of CH Bonds: A Versatile Strategy for CC Bond Formations

Angewandte Chemie International Edition, Год журнала: 2013, Номер 53(1), С. 74 - 100

Опубликована: Ноя. 8, 2013

Abstract Over the last decade, substantial research has led to introduction of an impressive number efficient procedures which allow selective construction CC bonds by directly connecting two different CH under oxidative conditions. Common these methodologies is generation reactive intermediates in situ activation both bonds. This strategy was introduced group Li as cross‐dehydrogenative coupling (CDC) and discloses waste‐minimized synthetic alternatives classic rely on use prefunctionalized starting materials. Review highlights recent progress field C C formations provides a comprehensive overview existing employed methodologies.

Язык: Английский

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Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis

Chemistry - A European Journal, Год журнала: 2010, Номер 16(37), С. 11212 - 11222

Опубликована: Авг. 25, 2010

Aromatic substrates with oxygen- and nitrogen-containing substituents undergo oxidative coupling alkynes alkenes under rhodium catalysis through regioselective C-H bond cleavage. Coordination of the to center is key activate bonds effectively. Various fused-ring systems can be constructed these reactions.

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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Functionalization of Organic Molecules by Transition‐Metal‐Catalyzed C(sp³)H Activation

Chemistry - A European Journal, Год журнала: 2010, Номер 16(9), С. 2654 - 2672

Опубликована: Фев. 8, 2010

Transition-metal-catalyzed C-H activation has recently emerged as a powerful tool for the functionalization of organic molecules. While many efforts have focused on arenes and heteroarenes by this strategy in past two decades, much less research been devoted to non-acidic bonds alkyl groups. This Minireview highlights recent work area, with particular emphasis synthetically useful methods.

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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Formal S_N‐Type Reactions in Rhodium(III)‐Catalyzed CH Bond Activation

Advanced Synthesis & Catalysis, Год журнала: 2014, Номер 356(7), С. 1443 - 1460

Опубликована: Май 5, 2014

Abstract (Pentamethylcyclopentadienyl)rhodium (RhCp*)‐catalyzed CH transformations have emerged as a prosperous field in bond activation. Recent advances this area significantly focused on the development of new strategies for CC and Cheteroatom formation that are characterized by novel reactivity RhCp* catalyst to undergo formal S N ‐type reactions with electrophilic substrates. This review is intended give an overview rather class RhCp*‐catalyzed transformations, covering recent bond‐forming reactions. The nature reaction partner these functionalization serves guideline throughout article and, combined selected descriptions mechanistic proposals, should emphasize general characteristics within class. magnified image

Язык: Английский

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Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Angewandte Chemie International Edition, Год журнала: 2010, Номер 49(14), С. 2486 - 2528

Опубликована: Март 23, 2010

Abstract Asymmetric catalysis with transition‐metal complexes is the basis for a vast array of stereoselective transformations and has changed face modern synthetic chemistry. Key to this success been design chiral ligands control regio‐, diastereo‐, enantioselectivity. Phosphoramidites have emerged as highly versatile readily accessible class ligands. Their modular structure enables formation ligand libraries easy fine‐tuning specific catalytic reaction. frequently show exceptional levels stereocontrol, their monodentate nature essential in combinatorial catalysis, where ligand‐mixture approach used. In Review, recent developments asymmetric phosphoramidites used are discussed, focus on carbon–carbon carbon–heteroatom bonds.

Язык: Английский

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