Cited by Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides

Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF₃ Complexes: A Modular Route to Functionalized Azacycles DOI

Kamal Bhatt,

Alafate Adili,

Andrew Tran

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range cyclic imine-BF

Language: Английский

Citations

Direct C1 Homologation of Carboxylic Acids: Free Radical Approach Enabled by Acridine Catalysis DOI

Zakhar M. Rubanov,

Vitalij V. Levin, Alexander D. Dilman

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Homologation of carboxylic acids with a tosylhydrazone reagent is described. The reaction performed using dual acridine/decatungstate photocatalytic system.

Language: Английский

Citations

N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins DOI

Boris A. van der Worp,

Tobias Ritter

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(6), P. 4736 - 4742

Published: Jan. 31, 2025

The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy potential cost-effectiveness. Herein, we present the first general method for direct, catalytic hydration unconjugated tri- disubstituted olefins. key advancement made possible by an oxidative (E*red = 2.15 V) N-H acridinium catalyst, which allowed functionalization alkenes that were previously unreactive in such transformations their high oxidation potential. developed protocol not limited but also enables other hydrofunctionalizations, as hydroetherifications, following same mechanistic pathway.

Language: Английский

Citations

Light‐Mediated Radical Addition to Azomethine Compounds: Novel Reactivity and Activation Modes DOI

Zakhar M. Rubanov,

Vitalij V. Levin, Alexander D. Dilman

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

Abstract Azomethines is a class of compounds, which have traditionally served as electrophilic substrates, but their reactions with radicals long been limited. Photocatalysis provided ample opportunities for promoting these reactions, wide variety reagents serving precursors radicals. Besides regular addition mode at the azomethine fragment, oxidative pathway, in C=N bond remains product, has become possible by proper selection redox catalyst. This review summarizes new developments this rapidly developing field over past five years. New concepts on activation towards radical attack are discussed.

Language: Английский

Citations

Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study DOI

Dillon R. L. Rickertsen,

Joshua D. Crow,

Tamal Das

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(19), P. 14574 - 14585

Published: Sept. 16, 2024

A class of in-situ generated Lewis acid (LA) activated acridine complexes is reported, which act as potent photochemical catalysts for the oxidation a variety protected secondary amines. Acridine/LA exhibit tunable excited state reduction potentials ranging from +2.07 to 2.38 V vs. SCE. The ytterbium triflate complex 3,6-di-t-butyl-9-mesitylacridine catalyzes Giese-type reaction Boc-protected amines with challenging conjugate acceptors such acrylates, that are inaccessible analogous acridinium (t-Bu-Mes-Acr⊕) catalyzed reaction. mechanism this was investigated using suite physical organic probes including intramolecular 13C kinetic isotope effects (KIEs), variable time normalization analysis (VTNA) kinetics, determination redox potentials, and computational studies. In by t-Bu-Mes-Acr⊕, mechanistic studies consistent single-electron transfer (SET) ground-state reduced t-Bu-Mes-Acr• α-keto radical intermediate first irreversible step in catalytic cycle. Intriguingly, we find acridine/LA better ground reductants (-0.72 -0.74 vs SCE) relative (-0.59 predict increased substrate reactivity stems lower energy barrier key SET event.

Language: Английский

Citations

Iterative One-Carbon Homologation of Unmodified Carboxylic Acids DOI

Emilie Wheatley,

Heorhii Melnychenko,

Mattia Silvi

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

The one-carbon homologation of carboxylic acids is a valuable route to construct families homologues, which play fundamental roles in chemistry and biology. However, known procedures are based on multistep sequences, use harsh conditions or limited scope. Thus, almost century after the discovery original Arndt–Eistert sequence, general method directly convert into their corresponding homologues remains elusive. Exploiting photoredox reactivity nitroethylene, we disclose practical visible-light-induced unmodified acids. Iterations procedure reveal an exceptionally tunable strategy for construction inert carbon spacers, opening new opportunities synthesis.

Language: Английский

Citations

Visible-Light-Driven Synthesis of N-Alkyl α-Amino Acid Derivatives from Unactivated Alkyl Bromides and In Situ Generated Imines DOI

Sen Yang,

Chaoying Qiu,

Hao Hu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 23, 2024

One-pot, multicomponent reactions are known for their green and efficient nature. We report a novel three-component reaction of alkyl amines, glyoxylates, unactivated bromides under visible-light-induced palladium catalysis, yielding

Language: Английский

Citations

Electricity-driven reductive coupling reaction of imines with N-(acyloxy)phthalimides DOI

X. Liu,

Leilei Feng

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 153, P. 155367 - 155367

Published: Nov. 14, 2024

Language: Английский

Citations