Photoinduced, additive- and photosensitizer-free multi-component synthesis of naphthoselenazol-2-amines with air in water

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7983 - 7987

Published: Jan. 1, 2023

An atom- and step-economical, efficient eco-friendly method for constructing naphthoselenazol-2-amines through a visible-light photocatalytic multi-component reaction under aqueous phase conditions is reported.

Language: Английский

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Synthesis of 1-(Halo)alkyl-3-heteroaryl Bicyclo[1.1.1]pentanes Enabled by a Photocatalytic Minisci-type Multicomponent Reaction

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 6247 - 6258

Published: April 10, 2024

Aryl-substituted bicyclo[1.1.1]pentane (BCP-aryl) derivatives represent the most important bioisosteres of biaryl scaffolds and widely exist in numerous complex pharmaceutical molecules. The current synthetic method limitations using only tertiary radical precursors, prefunctionalized heteroarenes, toxic transition metals, expensive photocatalysts make it urgent to develop a more simple practical protocol. To confront enrich Minisci-type chemistry, herein, we disclose photocatalytic multicomponent reaction for synthesis various (halo)alkyl BCP-aryls [1.1.1]propellane, alkyl halides, unfunctionalized heteroarenes as starting materials. Diverse kinds radicals (primary, secondary, carbons) derived from chlorides, bromides, fluoroalkyl iodides are very compatible this transformation. practicability is additionally boosted by product derivatizations late-stage functionalization pharmaceutically relevant mechanistic studies demonstrate that relay mechanism initiated consecutive photoinduced electron transfer (ConPET) process operation. We anticipate methodology would act useful tool biaryl-type drug derivatives, ultimately resulting great utility discovery program.

Language: Английский

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Energy-transfer photocatalysis for Minisci C–H (amino)alkylation of heteroarenes using oxime esters as dual-role reagents

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5122 - 5129

Published: Jan. 1, 2024

This study demonstrates a strategy involving photoinduced energy transfer for decarboxylative Minisci C–H (amino)alkylation of heteroarenes employing diverse oxime esters (from carboxylic acids) as (amino)alkylating reagents.

Language: Английский

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Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

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Copper-Catalyzed Radical Relay 1,3-Carbocarbonylation across Two Distinct C═C Bonds

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3014 - 3019

Published: March 28, 2024

The radical relay provides an effective paradigm for intermolecular assembly to achieve functionalization across remote chemical bonds. Herein, we report the first 1,3-carbocarbonylation of α-carbonyl alkyl bromides two separate C═C reaction is highly chemo- and regioselective, with C(sp3)–C(sp3) bonds one C═O bond formed in a single orchestrated operation. In addition, synthesis method under mild conditions using inexpensive copper as catalyst allows facile access structurally diverse products. plausible mechanism investigated through series control experiments, including trapping, clock critical intermediate 18O labeling experiment.

Language: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

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Photoinduced decarboxylative radical cascade alkylation/cyclization of benzimidazole derivatives with aliphatic carboxylic acid via ligand-to-iron charge transfer

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(33), P. 14684 - 14689

Published: Jan. 1, 2024

The photoinduced decarboxylative radical cascade alkylation/cyclization method with various benzimidazole moieties bearing unactivated alkenes efficiently synthesizes polycyclic benzimidazoles via LMCT processes.

Language: Английский

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Recent Advances in Photoinduced Radical Cascade Cyclizations Enabling Five-Membered N-Heterocycle Formation

Topics in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Visible-Light-Induced Desaturative β-Alkoxyoxalylation of N-Aryl Cyclic Amines with Difluoromethyl Bromides and H₂O Via a Triple Cleavage Process

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6773 - 6778

Published: Sept. 1, 2023

A visible-light-driven desaturative β-alkoxyoxalyation of N-aryl cyclic amines with difluoromethyl bromides and H2O has been reported. This tandem reaction is triggered by homolysis the C–Br bond to produce difuoroalkyl radical, which undergoes subsequent defluorinated β-alkoxyoxalylation cascades afford a wide range β-ketoester/ketoamides substituted enamines. The prominent feature this contains photocatalyst-free, transition-metal free, mild conditions. 18O labeling experiment disclosed that oxygen source carbonyl unit.

Language: Английский

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Photoinduced desaturative β-C(sp³)–H amidation of N-phenylpiperidine with phthalimide driven by electron donor–acceptor complexes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4758 - 4763

Published: Jan. 1, 2023

A photocatalytic method for desaturative C(sp 3 )–H amidation of N -phenylpiperidine under external photocatalyst- and transition metal-free conditions.

Language: Английский

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