Electrochemical strategies for C–H functionalization and C–N bond formation

Chemical Society Reviews, Год журнала: 2018, Номер 47(15), С. 5786 - 5865

Опубликована: Янв. 1, 2018

This review provides an overview of the use electrochemistry as appealing platform for expediting carbon–hydrogen functionalization and carbon–nitrogen bond formation.

Язык: Английский

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Catalytic Applications of Vanadium: A Mechanistic Perspective

Chemical Reviews, Год журнала: 2018, Номер 119(4), С. 2128 - 2191

Опубликована: Окт. 8, 2018

The chemistry of vanadium has seen remarkable activity in the past 50 years. In present review, reactions catalyzed by homogeneous and supported complexes from 2008 to 2018 are summarized discussed. Particular attention is given mechanistic kinetics studies vanadium-catalyzed including oxidations alkanes, alkenes, arenes, alcohols, aldehydes, ketones, sulfur species, as well oxidative C–C C–O bond cleavage, carbon–carbon formation, deoxydehydration, haloperoxidase, cyanation, hydrogenation, dehydrogenation, ring-opening metathesis polymerization, oxo/imido heterometathesis. Additionally, insights into heterogeneous catalysis provided when parallels can be drawn literature.

Язык: Английский

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Recent Advances in Hydrometallation of Alkenes and Alkynes via the First Row Transition Metal Catalysis

Chinese Journal of Chemistry, Год журнала: 2018, Номер 36(11), С. 1075 - 1109

Опубликована: Авг. 20, 2018

Abstract Hydrometallation of alkenes and alkynes provides a straightforward route to access alkyl‐ or alkenyl‐metal reagents, which have wide range applications in organic transformations. In recent years, the first row transition metals (such as copper, nickel, cobalt, iron, etc .) emerged high activity selectivity this area with aid variety ligands. This review covers advances hydrometallation minimally functionalized unsaturated C—C bonds (including alkenes, alkynes, dienes, allenes, enynes, .), well transformations involving catalytic process via metal catalysis.

Язык: Английский

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A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Science, Год журнала: 2018, Номер 360(6392), С. 1010 - 1014

Опубликована: Июнь 1, 2018

Transition metal-catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis long considered a privileged platform due to propensity of high-valent undergo reductive elimination with wide variety coupling fragments. However, sluggish nature oxidative addition limited copper's capacity broadly facilitate haloarene protocols. Here, we demonstrate that problem can be overcome an aryl radical-capture mechanism, wherein radical is generated through silyl halogen abstraction. This strategy was applied general trifluoromethylation bromides dual copper-photoredox catalysis. Mechanistic studies support formation open-shell species.

Язык: Английский

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Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future

Organometallics, Год журнала: 2018, Номер 38(1), С. 3 - 35

Опубликована: Ноя. 27, 2018

Cross-coupling reactions, which were discovered almost 50 years ago, are widely used in both industry and academia. Even though cross-coupling reactions now represent mature technology, there is still a significant amount of research this area that aims to improve the scope these develop more efficient catalysts, make practical. In tutorial, brief background provided, then major advances over last 20 described. These include development improved ligands precatalysts for extension much wider range electrophiles. For example, common with sp3-hybridized electrophiles as well ester, amide, ether, aziridine substrates. many modern substrates, traditional palladium-based catalysts less than systems based on first-row transition metals such nickel. Conventional have also inspired related cross-electrophile decarboxylative couplings metallaphotoredox chemistry. The new probably at same stage 30 tutorial highlights how strategies may be applicable making

Язык: Английский

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Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2292 - 2352

Опубликована: Дек. 9, 2021

The halogen-atom transfer (XAT) is one of the most important and applied processes for generation carbon radicals in synthetic chemistry. In this review, we summarize highlight aspects associated with XAT impact it has had on photochemistry photocatalysis. organization material starts analysis mechanistic then follows a subdivision based nature reagents used halogen abstraction. This review aims to provide general overview fundamental concepts main agents involved objective offering tool understand facilitate development new radical strategies.

Язык: Английский

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Mechanistic Development and Recent Applications of the Chan–Lam Amination

Chemical Reviews, Год журнала: 2019, Номер 119(24), С. 12491 - 12523

Опубликована: Ноя. 22, 2019

Transition metal-mediated formation of C-N bonds is an essential synthetic methodology. The discovery the Chan-Lam amination provided a bond forming process that was mild, convenient, and inexpensive, offering alternative to complementary methods using other transition metals (TMs). Over past 20 years, this reaction has seen considerable development in its scope application, uptake into industry, understanding mechanism. This review provides account amination, highlighting progress notable examples application since 2011. Focus given evolution mechanistic selected applications methodology within medicinal chemistry.

Язык: Английский

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Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis

Nature, Год журнала: 2018, Номер 559(7712), С. 83 - 88

Опубликована: Июнь 18, 2018

Язык: Английский

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The 25th Anniversary of the Buchwald–Hartwig Amination: Development, Applications, and Outlook

Organic Process Research & Development, Год журнала: 2019, Номер 23(8), С. 1478 - 1483

Опубликована: Июль 2, 2019

The palladium-catalyzed cross-coupling of amines and aryl (pseudo)halides, now commonly known as the Buchwald–Hartwig amination, was first reported 25 years ago. Since simultaneous breakthrough reports Buchwald Hartwig in 1995, this reaction has transformed way synthetic chemists think about synthesizing aromatic amines. In highlight article, a short showcasing discussion genesis is provided, along with selected examples showing impact transformation chemistry both academic industrial settings.

Язык: Английский

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First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

Chemical Reviews, Год журнала: 2021, Номер 121(21), С. 13238 - 13341

Опубликована: Окт. 7, 2021

Organoboron reagents represent a unique class of compounds because their utility in modern synthetic organic chemistry, often affording unprecedented reactivity. The transformation the carbon–boron bond into carbon–X (X = C, N, and O) stereocontrolled fashion has become invaluable medicinal agrochemistry, natural products chemistry as well materials science. Over past decade, first-row d-block transition metals have increasingly widely used catalysts for formation bond, traditionally catalyzed by expensive precious metals. This recent focus on alternative enabled growth fundamental methods organoboron chemistry. review surveys current state-of-the-art use element-based bonds.

Язык: Английский

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