Metallaphotoredox-Catalyzed Cross-Electrophile Csp3–Csp3 Coupling of Aliphatic Bromides DOI

Russell T. Smith,

Xiaheng Zhang, Juan A. Rincón

и другие.

Journal of the American Chemical Society, Год журнала: 2018, Номер 140(50), С. 17433 - 17438

Опубликована: Дек. 5, 2018

A strategy for the installation of small alkyl fragments onto pharmaceutically relevant aliphatic structures has been established via metallaphotoredox catalysis. Herein, we report that tris(trimethylsilyl)silanol can be employed as an effective halogen abstraction reagent that, in combination with photoredox and nickel catalysis, allows a generic approach to Csp3–Csp3 cross-electrophile coupling. In this study, demonstrate variety drug-like groups successfully coupled number commercially available electrophiles, including methyl tosylate strained cyclic bromides. Moreover, union two secondary carbon centers, long-standing challenge organic molecule construction, accomplished wide array structural formats. Last, technology selectively merged Csp2–Csp3 aryl–alkyl couplings build systems highly modular fashion.

Язык: Английский

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis DOI
Amy Chan, Ian B. Perry, Noah B. Bissonnette

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 1485 - 1542

Опубликована: Ноя. 18, 2021

The merger of photoredox catalysis with transition metal catalysis, termed metallaphotoredox has become a mainstay in synthetic methodology over the past decade. Metallaphotoredox combined unparalleled capacity for bond formation broad utility photoinduced electron- and energy-transfer processes. Photocatalytic substrate activation allowed engagement simple starting materials metal-mediated bond-forming Moreover, electron or energy transfer directly key organometallic intermediates provided novel modes entirely complementary to traditional catalytic platforms. This Review details contextualizes advancements molecule construction brought forth by metallaphotocatalysis.

Язык: Английский

Процитировано

1149

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts DOI Creative Commons
Daniel Kaiser, Immo Klose,

Rik Oost

и другие.

Chemical Reviews, Год журнала: 2019, Номер 119(14), С. 8701 - 8780

Опубликована: Июнь 25, 2019

Organosulfur compounds have long played a vital role in organic chemistry and the development of novel chemical structures architectures. Prominent among these organosulfur are those involving sulfur(IV) center, which been subject countless investigations over more than hundred years. In addition to list textbook sulfur-based reactions, there has sustained interest organosulfur(IV) recent Of particular within is ease with synthetic chemist can effect wide range transformations through either bond formation or cleavage at sulfur. This review aims cover developments past decade molecules provide insight into both reactions critically rely on this versatile element diverse scaffolds that thereby be synthesized.

Язык: Английский

Процитировано

698

Copper’s rapid ascent in visible-light photoredox catalysis DOI Open Access
Asik Hossain, Aditya Bhattacharyya, Oliver Reiser

и другие.

Science, Год журнала: 2019, Номер 364(6439)

Опубликована: Май 2, 2019

Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of processes capitalizes on precious ruthenium(II) or iridium(III) complexes that serve as single-electron reductants oxidants in their photoexcited states. As low-cost alternative, organic dyes are also frequently used but general suffer from lower photostability. Copper-based photocatalysts rapidly emerging, offering not only economic and ecological advantages otherwise inaccessible inner-sphere mechanisms, which have been successfully applied challenging transformations. Moreover, the combination conventional with copper(I) copper(II) salts has emerged an efficient dual catalytic system for cross-coupling

Язык: Английский

Процитировано

567

Visible Light-Induced Transition Metal Catalysis DOI
Kelvin Pak Shing Cheung, Sumon Sarkar, Vladimir Gevorgyan

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 1543 - 1625

Опубликована: Окт. 8, 2021

In recent years, visible light-induced transition metal catalysis has emerged as a new paradigm in organic photocatalysis, which led to the discovery of unprecedented transformations well improvement known reactions. this subfield complex serves double duty by harvesting photon energy and then enabling bond forming/breaking events mostly via single catalytic cycle, thus contrasting established dual photocatalysis an exogenous photosensitizer is employed. addition, approach often synergistically combines catalyst–substrate interaction with photoinduced process, feature that uncommon conventional photoredox chemistry. This Review describes early development advances emerging field.

Язык: Английский

Процитировано

548

Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides DOI
Timothée Constantin, Margherita Zanini, Alessio Regni

и другие.

Science, Год журнала: 2020, Номер 367(6481), С. 1021 - 1026

Опубликована: Фев. 27, 2020

Organic halides are important building blocks in synthesis, but their use (photo)redox chemistry is limited by low reduction potentials. Halogen-atom transfer remains the most reliable approach to exploit these substrates radical processes despite its requirement for hazardous reagents and initiators such as tributyltin hydride. In this study, we demonstrate that α-aminoalkyl radicals, easily accessible from simple amines, promote homolytic activation of carbon-halogen bonds with a reactivity profile mirroring classical tin radicals. This strategy conveniently engages alkyl aryl wide range redox transformations construct sp3-sp3, sp3-sp2, sp2-sp2 carbon-carbon under mild conditions high chemoselectivity.

Язык: Английский

Процитировано

439

Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis DOI
Fabio Juliá, Timothée Constantin, Daniele Leonori

и другие.

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

Процитировано

388

Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents DOI Creative Commons
Jonathan D. Bell, John A. Murphy

Chemical Society Reviews, Год журнала: 2021, Номер 50(17), С. 9540 - 9685

Опубликована: Янв. 1, 2021

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

Язык: Английский

Процитировано

340

Chemistry glows green with photoredox catalysis DOI Creative Commons
Giacomo E. M. Crisenza, Paolo Melchiorre

Nature Communications, Год журнала: 2020, Номер 11(1)

Опубликована: Фев. 6, 2020

Can organic chemistry mimic nature in efficiency and sustainability? Not yet, but recent developments photoredox catalysis animated the synthetic field, providing greener opportunities for industry academia.

Язык: Английский

Процитировано

335

Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis DOI Creative Commons

Megan Amy Bryden,

Eli Zysman‐Colman

Chemical Society Reviews, Год журнала: 2021, Номер 50(13), С. 7587 - 7680

Опубликована: Янв. 1, 2021

Organic compounds that show Thermally Activated Delayed Fluorescence (TADF) have become wildly popular as next generation emitters in organic light-emitting diodes (OLEDs), but since 2016, received significant and increasing attention photocatalysts.

Язык: Английский

Процитировано

333

Visible light photocatalysis in the late-stage functionalization of pharmaceutically relevant compounds DOI
Rolando Cannalire, Sveva Pelliccia, Luca Sancineto

и другие.

Chemical Society Reviews, Год журнала: 2020, Номер 50(2), С. 766 - 897

Опубликована: Дек. 22, 2020

Recent developments and future prospects of visible-light photocatalysis in the late-stage functionalization pharmaceuticals natural bioactive compounds.

Язык: Английский

Процитировано

332