Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp³)–H/C(sp³)–H and C(sp³)–H/C(sp²)–H via Intermolecular HAT

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4264 - 4269

Published: June 2, 2023

Cross-dehydrogenative coupling has emerged as a robust tool to construct C–C and C–heteroatom bonds. Herein, we reported an interesting visible-light-mediated radical CDC of C(sp3)–H/C(sp3)–H C(sp3)–H/C(sp2)–H, enabled by phenyl guided intermolecular HAT process. This strategy allowed the efficient wide range inert C(sp3)–H C(sp2)–H with α-N amines in good regioselectivities yields. Mechanistic studies indicate that EDA complex triggered

Language: Английский

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Electron Donor-Acceptor (EDA) Complex-Driven Activation of N-α C—H Bonds

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 559 - 559

Published: Jan. 1, 2025

Language: Английский

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Selective α-oxidation of amides via visible-light-driven iron catalysis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1205 - 1212

Published: Jan. 1, 2024

Hydroxyl radical-induced selective N -α C(sp 3 )–H bond oxidation of amides was investigated via the visible-light-induced homolysis (VLIH) iron( iii ) complexes.

Language: Английский

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Visible-Light-Mediated Aerobic α-Oxygenation of Tetrahydroisoquinolines and Isoindolines Without External Photocatalysts

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 743 - 743

Published: Feb. 6, 2025

A visible-light-mediated strategy for the direct oxygenation of N-substituted tetrahydroisoquinolines and isoindolines to corresponding benzo-fused lactams under clean conditions without using any external photocatalysts has been developed. The reaction was performed in presence a catalytic amount base oxygen. Mechanistic studies reveal that is initiated by substrates themselves as photosensitizers. Additionally, BHT could be used buffer-like additive improve selectivity product yield this photo-oxidation process.

Language: Английский

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Visible light-driven photocatalytic sulfonative oxidation of benzyl secondary amines

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(19), P. 3904 - 3909

Published: Jan. 1, 2024

This protocol developed α-oxidation and sulfonation of benzyl secondary amines using Eosin Y or Ir( iii ) as a photocatalyst in the presence O 2 green oxidant.

Language: Английский

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Visible light-induced metal-free chemoselective oxidative cleavage of benzyl C–heteroatom (N, S, Se) bonds utilizing organoboron photocatalysts

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(89), P. 13344 - 13347

Published: Jan. 1, 2023

We have established a photooxidation system, which can realize formal carbonylation of C–heteroatom (N, S, Se) bonds.

Language: Английский

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Dehydrogenative Electrochemical Synthesis of N‐Aryl‐3,4‐Dihydroquinolin‐2‐ones by Iodine(III)‐Mediated Coupling Reaction

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(7)

Published: Nov. 29, 2023

Abstract Electrochemically generated hypervalent iodine(III) species are powerful reagents for oxidative C−N coupling reactions, providing access to valuable N‐heterocycles. A new electrocatalytic iodine(III)‐mediated in‐cell synthesis of 1 H ‐ N ‐aryl‐3,4‐dihydroquinolin‐2‐ones by dehydrogenative bond formation is presented. Catalytic amounts the redox mediator, a low supporting electrolyte concentration and recycling solvent used make this method sustainable alternative electrochemical ex‐cell or conventional approaches. Furthermore, inexpensive, readily available electrode materials simple galvanostatic set‐up applied. The broad functional group tolerance could be demonstrated synthesizing 23 examples in yields up 96 %, with one reaction being performed on 10‐fold higher scale. Based obtained results sound mechanism proposed.

Language: Английский

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Decarboxylative Aminomethylation of Ferulic Acids via Visible‐Light‐Promoted Flavin Photocatalysis and its Application in the Synthesis of Anti‐Inflammatory Lead Compounds

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4702 - 4708

Published: Aug. 8, 2024

Abstract Herein, we report a protocol for the direct visible‐light‐promoted decarboxylative aminomethylation of ferulic acid with N‐aryl tetrahydroisoquinolines under air atmosphere. The current uses naturally available as coupling partner, inexpensive organic photocatalyst riboflavin tetraacetate (RFTA) and molecular oxygen oxidant, which is suitable late‐stage functionalization complex nitrogen‐containing molecules. This methodology further demonstrated its utility by protecting‐group‐free semi‐synthesis natural alkaloids maclekarpine E assessing anti‐inflammatory activity analogues.

Language: Английский

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Visible Light Mediated Chemoselective Hydroxylation of Benzylic Methylenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2656 - 2664

Published: Feb. 7, 2024

We have developed a metal-free photocatalytic selective hydroxylation of benzylic methylenes to secondary alcohols. This approach utilizes low-cost eosin Y as photocatalyst, O2 green oxidant, and inexpensive triethylamine inhibitor for overoxidation. The mild reaction conditions enable the production alcohols with 56–95% yields, making it promising environmental-friendly method synthesis from methylenes.

Language: Английский

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Visible light-mediated photocatalyst-free N-demethylation of aryl tertiary amines

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 124, P. 154585 - 154585

Published: June 3, 2023

Language: Английский

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