Anodically Coupled Electrolysis for the Heterodifunctionalization of Alkenes DOI
Ke‐Yin Ye,

Gisselle Pombar,

Niankai Fu

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(7), P. 2438 - 2441

Published: Feb. 6, 2018

The emergence of new catalytic strategies that cleverly adopt concepts and techniques frequently used in areas such as photochemistry electrochemistry has yielded a myriad organic reactions would be challenging to achieve using orthodox methods. Herein, we discuss the strategic use anodically coupled electrolysis, an electrochemical process combines two parallel oxidative events, complementary approach existing methods for redox transformations. Specifically, demonstrate electrolysis regio- chemoselective chlorotrifluoromethylation alkenes.

Language: Английский

Visible‐Light Photocatalysis: Does It Make a Difference in Organic Synthesis? DOI Open Access
Leyre Marzo, Santosh K. Pagire, Oliver Reiser

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 57(32), P. 10034 - 10072

Published: Feb. 21, 2018

Visible-light photocatalysis has evolved over the last decade into a widely used method in organic synthesis. Photocatalytic variants have been reported for many important transformations, such as cross-coupling reactions, α-amino functionalizations, cycloadditions, ATRA or fluorinations. To help chemists select photocatalytic methods their synthesis, we compare this Review classical and procedures selected classes of reactions highlight advantages limitations. In cases, proceed under milder reaction conditions, typically at room temperature, stoichiometric reagents are replaced by simple oxidants reductants, air, oxygen, amines. Does visible-light make difference synthesis? The prospect shuttling electrons back forth to substrates intermediates selectively transfer energy through visible-light-absorbing photocatalyst holds promise improve current radical chemistry open up new avenues accessing reactive species hitherto unknown, especially merging with organo- metal catalysis.

Language: Английский

Citations

1808

The Hitchhiker’s Guide to Flow Chemistry DOI
Matthew B. Plutschack, Bartholomäus Pieber, Kerry Gilmore

et al.

Chemical Reviews, Journal Year: 2017, Volume and Issue: 117(18), P. 11796 - 11893

Published: June 1, 2017

Flow chemistry involves the use of channels or tubing to conduct a reaction in continuous stream rather than flask. equipment provides chemists with unique control over parameters enhancing reactivity some cases enabling new reactions. This relatively young technology has received remarkable amount attention past decade many reports on what can be done flow. Until recently, however, question, "Should we do this flow?" merely been an afterthought. review introduces readers basic principles and fundamentals flow critically discusses recent accounts.

Language: Английский

Citations

1677

Organic synthesis provides opportunities to transform drug discovery DOI

David C. Blakemore,

Luis C. Misal Castro, Ian Churcher

et al.

Nature Chemistry, Journal Year: 2018, Volume and Issue: 10(4), P. 383 - 394

Published: March 22, 2018

Language: Английский

Citations

1252

Electrochemical strategies for C–H functionalization and C–N bond formation DOI Creative Commons
Markus D. Kärkäs

Chemical Society Reviews, Journal Year: 2018, Volume and Issue: 47(15), P. 5786 - 5865

Published: Jan. 1, 2018

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

Language: Английский

Citations

880

Late-stage C–H functionalization offers new opportunities in drug discovery DOI
Lucas Guillemard, Nikolaos Kaplaneris, Lutz Ackermann

et al.

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(8), P. 522 - 545

Published: July 13, 2021

Language: Английский

Citations

582

Alkyl Carbon–Carbon Bond Formation by Nickel/Photoredox Cross‐Coupling DOI
John A. Milligan, James P. Phelan, Shorouk O. Badir

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(19), P. 6152 - 6163

Published: Oct. 6, 2018

The union of photoredox and nickel catalysis has resulted in a renaissance radical chemistry as well the use nickel-catalyzed transformations, specifically for carbon-carbon bond formation. Collectively, these advances address longstanding challenge late-stage cross-coupling functionalized alkyl fragments. Empowered by notion that photocatalytically generated radicals readily undergo capture Ni complexes, wholly new feedstocks have been realized. Herein, we highlight recent developments several types cross-couplings are accessible exclusively through this approach.

Language: Английский

Citations

563

Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development DOI Creative Commons
Jennifer K. Matsui, Simon B. Lang,

Drew R. Heitz

et al.

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(4), P. 2563 - 2575

Published: March 14, 2017

Photoredox catalysis has experienced a revitalized interest from the synthesis community during past decade. For example, photoredox/Ni dual protocols have been developed to overcome several inherent limitations of palladium-catalyzed cross-couplings by invoking single-electron transmetalation pathway. This Perspective highlights advances made our laboratory since inception cross-coupling benzyltrifluoroborates with aryl bromides. In addition broadening scope trifluoroborate coupling partners, research using readily oxidized hypervalent silicates as radical precursors that demonstrate functional group compatibility is highlighted. The pursuit electrophilic partners beyond (hetero)aryl bromides also led incorporation new classes C(sp2)-hybridized substrates into light-mediated cross-coupling. Advances expand toolbox utilizing feedstock chemicals (e.g., aldehydes) access radicals were previously inaccessible trifluoroborates and are emphasized. Additionally, organic photocatalysts investigated replacements for their expensive iridium- ruthenium-based counterparts. Lastly, net C–H functionalization partner in an effort improve atom economy presented. An underlying theme all these studies value generating catalytic manner, rather than stoichiometrically.

Language: Английский

Citations

554

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

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 1543 - 1625

Published: Oct. 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.

Language: Английский

Citations

549

Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks DOI Creative Commons

James W. B. Fyfe,

Allan J. B. Watson

Chem, Journal Year: 2017, Volume and Issue: 3(1), P. 31 - 55

Published: July 1, 2017

Language: Английский

Citations

525

Illuminating Photoredox Catalysis DOI Open Access
Rory C. McAtee, Edward J. McClain, Corey R. J. Stephenson

et al.

Trends in Chemistry, Journal Year: 2019, Volume and Issue: 1(1), P. 111 - 125

Published: Feb. 23, 2019

Language: Английский

Citations

432