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

Open-Air Alkylation Reactions in Photoredox-Catalyzed DNA-Encoded Library Synthesis DOI
James P. Phelan, Simon B. Lang, Jaehoon Sim

et al.

Journal of the American Chemical Society, Journal Year: 2019, Volume and Issue: 141(8), P. 3723 - 3732

Published: Feb. 12, 2019

DNA-encoded library (DEL) technology is a powerful tool commonly used by the pharmaceutical industry for identification of compounds with affinity to biomolecular targets. Success in this endeavor lies sampling diverse chemical libraries. However, current DELs tend be deficient C(sp3) carbon counts. We report unique solutions challenge increasing both diversity these libraries and their counts merging Ni/photoredox dual catalytic C(sp2)-C(sp3) cross-coupling as well photoredox-catalyzed radical/polar crossover alkylation protocols DELs. The successful integration multiple classes radical sources enables rapid incorporation set alkyl fragments.

Language: Английский

Citations

285

Catalysis with Palladium Complexes Photoexcited by Visible Light DOI
Padon Chuentragool, Daria Kurandina, Vladimir Gevorgyan

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(34), P. 11586 - 11598

Published: Jan. 2, 2019

Abstract Palladium catalysis induced by visible light is an emerging field of catalysis. In contrast to classical reactions catalyzed Pd complexes in the ground state, which mostly proceed through two‐electron redox processes, mechanisms these new methods based on photoexcited usually operate transfer a single electron. Such processes lead putative hybrid Pd/radical species, exhibit both radical and Pd‐type reactivity. This Minireview highlights recent progress this rapidly growing area.

Language: Английский

Citations

254

Enantioselective Radical Reactions Using Chiral Catalysts DOI
Shovan Mondal, Frédéric Dumur, Didier Gigmès

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(6), P. 5842 - 5976

Published: Jan. 24, 2022

Benefiting from the impressive increase in fundamental knowledge, last 20 years have shown a continuous burst of new ideas and consequently plethora catalytic methods for enantioselective radical reactions. This review aims to provide complete survey progress achieved over this latter period. The first part focuses on use chiral organocatalysts, these include catalysts covalently linked substrate those that interact with by weaker interactions like hydrogen bonds. second is devoted transition-metal redox catalysis which organized according increasing atomic number first-row transition metals (Ti, Cr, Fe, Mn, Co, Ni, Cu). Bioinspired manganese- iron-mediated hydroxylations oxidations are also discussed. A specific section dedicated reactivity Ru, Rh, Ir complexes as Lewis acids special focus at metal. Absorption photons result different events such energy transfer, single-electron hydrogen-atom transfer facilitating formation radicals. Organocatalysis has been successfully combined photocatalysts, opened pathways enlarging precursors available. merger photocatalysis organo- or metalla-photocatalysis brought novelty allowed discovery large original transformations. enzyme-catalyzed reactions involving intermediates largely benefit visible-light irradiation included review. provides comprehensive inventory goal detailing reaction mechanisms involved transformations any nonspecialist could find their own creativity invent yet unknown applications.

Language: Английский

Citations

253

1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis DOI Creative Commons

Álvaro Gutiérrez‐Bonet,

John C. Tellis, Jennifer K. Matsui

et al.

ACS Catalysis, Journal Year: 2016, Volume and Issue: 6(12), P. 8004 - 8008

Published: Oct. 27, 2016

A Ni/photoredox dual catalytic cross-coupling is disclosed in which a diverse range of (hetero)aryl bromides are used as electrophiles, with 1,4-dihydropyridines serving precursors to Csp3-centered alkyl radical coupling partners. The reported method characterized by its extremely mild reaction conditions, enabling access underexplored cores.

Language: Английский

Citations

245

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

Citations

235