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   Articles with "polar crossover" as a keyword



Merging New and Old Concepts: Tandem Oxidative Radical‐Polar Crossover Ritter Amidation via Multicomponent Photo‐ and Electrochemical Processes

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recommendations! Published in 2024 at "European Journal of Organic Chemistry"

DOI: 10.1002/ejoc.202400840

Abstract: Nitrogen‐containing drug molecules and pharmaceuticals are ubiquitous, rendering the construction of C–N bonds a crucial target in methodology development. The Ritter reaction is a well‐established method for accessing C–N bonds by generating amide functionality through… read more here.

Keywords: reaction; chemistry; polar crossover; radical polar ... See more keywords

Photoredox/Copper Dual-Catalyzed Benzylic C-H Esterification via Radical-Polar Crossover.

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recommendations! Published in 2022 at "Organic letters"

DOI: 10.1021/acs.orglett.2c00763

Abstract: Herein, we report a distinctive photoredox/copper dual-catalyzed esterification of benzylic C-H bonds through the combination of photoredox-mediated hydrogen atom transfer and Cu(II)-mediated radical-polar crossover. This methodology demonstrates a high functional group tolerance (>40 examples) and… read more here.

Keywords: polar crossover; dual catalyzed; copper dual; photoredox copper ... See more keywords

Synthesis of Indeno[1,2-c]furans via Cobalt-Catalyzed Radical-Polar Crossover [3 + 2] Cycloaddition of o-Alkynylaryl β-Dicarbonyls.

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recommendations! Published in 2022 at "Organic letters"

DOI: 10.1021/acs.orglett.2c03297

Abstract: Fused polycyclic furans are privileged structural scaffolds in materials chemistry, including organic semiconductors. Specifically, indeno[1,2-c]furans are an interesting type of polycyclic furans featuring a fused furan and indenone framework. Unfortunately, limited studies on their photophysical… read more here.

Keywords: cobalt catalyzed; polar crossover; catalyzed radical; indeno furans ... See more keywords
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Photoredox-Catalyzed Multicomponent Synthesis of Functionalized γ-Amino Butyric Acids via Reductive Radical Polar Crossover.

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recommendations! Published in 2023 at "Organic letters"

DOI: 10.1021/acs.orglett.3c00991

Abstract: Multicomponent radical polar crossover (RPC) reactions are useful for leveraging both radical and polar bond-forming steps to rapidly build molecular complexity in a single transformation. However, multicomponent RPC reactions that utilize carbonyl π-bond electrophiles are… read more here.

Keywords: functionalized amino; polar crossover; amino butyric; photoredox catalyzed ... See more keywords

Radical-Polar Crossover Enabled Photoredox 1,2-Carbosulfinylation of Alkenes with N-Sulfinyltritylamine.

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recommendations! Published in 2025 at "Organic letters"

DOI: 10.1021/acs.orglett.5c04649

Abstract: The alkylation of N-sulfinylamines has emerged as a straightforward and promising platform for the construction of sulfinamides. Nevertheless, extant strategies─whether through two-electron nucleophilic addition or single-electron radical pathways─remain confined to two-component reactions, exhibiting intrinsic constraints… read more here.

Keywords: polar crossover; radical polar; photoredox carbosulfinylation; crossover enabled ... See more keywords

Hydroarylation of Arenes via Reductive Radical-Polar Crossover.

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recommendations! Published in 2020 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.0c03926

Abstract: A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where… read more here.

Keywords: hydroarylation; radical polar; polar crossover; reductive radical ... See more keywords

Radical-Polar Crossover Catalysis with a d0 Metal Enabled by a Redox-Active Ligand.

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recommendations! Published in 2022 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.2c09114

Abstract: Radical-polar crossover mechanisms are invoked in numerous late transition metal and photocatalyzed reactions. To the best of our knowledge, reductive radical-polar crossover mechanisms are not invoked for group 3 early transition metals due to their… read more here.

Keywords: polar crossover; metal; redox active; radical polar ... See more keywords

Experimental Evidence for Radical-Polar Crossover in Competition with, Rather Than Preceding, Alkene Formation by Microbial Ethylene-Forming Enzyme.

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recommendations! Published in 2025 at "Journal of the American Chemical Society"

DOI: 10.1021/jacs.5c13787

Abstract: Ethylene-forming enzyme (EFE) catalyzes a reaction that sets it apart from other iron(II)- and 2-oxoglutarate-dependent (Fe/2OG) oxygenases. In this reaction, all four oxidizing equivalents of O2 are unleashed upon 2OG, fragmenting it to ethylene (from… read more here.

Keywords: ethylene; polar crossover; radical polar; ethylene forming ... See more keywords

A three-component difunctionalization of N-alkenyl amides via organophotoredox radical-polar crossover.

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recommendations! Published in 2022 at "Chemical communications"

DOI: 10.1039/d2cc04101d

Abstract: Herein, we report a three-component organophotoredox coupling of N-alkenyl amides with α-bromocarbonyls and various nucleophiles. This transition metal-free difunctionalization protocol installs sequential C-C and C-Y (Y = S/O/N) bonds in alkenes. This reaction works with… read more here.

Keywords: amides via; difunctionalization; polar crossover; alkenyl amides ... See more keywords

Visible light-induced C(sp3)-H azolation of ethers via radical-polar crossover.

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recommendations! Published in 2024 at "Chemical communications"

DOI: 10.1039/d3cc06210d

Abstract: Reported herein is a photochemical strategy for C(sp3)-H azolation of ethers via a hydrogen-atom transfer and radical-polar crossover process, offering efficient access to valuable N-alkylated azoles under visible-light irradiation. The protocol is metal-free and photocatalyst-free,… read more here.

Keywords: polar crossover; visible light; radical polar; azolation ethers ... See more keywords

Photoredox Radical/Polar Crossover Enables C-H gem-Difunctionalization of 1,3-Benzodioxoles for the Synthesis of Monofluorocyclohexenes

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recommendations! Published in 2023 at "Chemical Science"

DOI: 10.1039/d3sc00912b

Abstract: A photocatalytic C–H gem-difunctionalization of 1,3-benzodioxoles with two different alkenes for the synthesis of highly functionalized monofluorocyclohexenes is described. Using 4CzIPN as the photocatalyst, the direct single electron oxidation of 1,3-benzodioxoles allows their defluorinative coupling… read more here.

Keywords: radical polar; polar crossover; difunctionalization benzodioxoles; gem difunctionalization ... See more keywords