Photochemical aerobic sulfonylation–cyclization–selenylation to indole-fused medium-sized N-heterocycles in 2-Me-THF

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We report a novel visible-light-induced sulfonylation cyclization and aerobic selenylation reaction for the rapid construction of highly functionalized indole-fused medium-sized diazepinones with biomass feedstock 2-Me-THF as medium.

Language: Английский

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Rhodium(iii)-catalyzed regioselective C2-alkenylation of indoles with CF₃-imidoyl sulfoxonium ylides to give multi-functionalized enamines using a migratable directing group

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(3), P. 318 - 321

Published: Dec. 7, 2022

A rhodium(III)-catalyzed regioselective C2-alkenylation of indoles for the construction α-CF3 substituted enamines has been developed, which utilizes CF3-imidoyl sulfoxonium ylides (TFISYs) as alkenylating agents first time. wide array indolyl- and trifluoromethyl-decorated enamine derivatives have assembled in moderate to good yields.

Language: Английский

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Visible-Light-Induced Sulfonylation Cyclization to Generate Indole-Fused Medium-Sized N-Heterocycles in 2-Me-THF

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

A novel visible-light-induced sulfonylation cyclization to indole-fused medium-sized N-heterocycles was established under room temperature with biomass-derived 2-Me-THF as the solvent. This reaction proceeds in absence of external photocatalyst, additive, metal salts, and base. Broad substrate scope, good functional group compatibility, large-scale synthesis derivatization via iodination, nitration, chlorination, cyanation, selenylation demonstrate utility this protocol. radical route proposed based on inhibition experiments, visible-light irradiation on-off test, apparent quantum efficiency calculation, UV-vis absorption spectroscopic studies.

Language: Английский

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Pd(II)-Catalyzed [5 + 2] Cyclization of N-Triflyl Aryl Indoles and α,γ-Substituted Allenoates: A Route to Indole-Fused Benzodiazepines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(34), P. 6246 - 6250

Published: Aug. 17, 2023

A Pd(II)-catalyzed [5 + 2] annulation between N-triflyl aryl indoles and α,γ-substituted allenoates for the synthesis of indole-fused benzodiazepines is reported. This protocol highly efficient when N-acetylated valine amino acid DMSO have been used as ligand cosolvent, respectively. The substrate scope can be further extended to disubstituted allenoates. reaction mechanism has proposed based on mechanistic studies. Mechanistically, accelerates C-H activation C(sp2)-H bond. Consequent cyclopalladation leads formation a six-membered palladacycle. Subsequent coordination migratory insertion an allenoate forms possible eight-membered intermediate. Reductive elimination followed by [1,3]-H shift results in benzodiazepines.

Language: Английский

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Rhodium(III)-Catalyzed Sequential Cyclization of Enaminones with 1,3-Dienes via C–H Activation for the Synthesis of Fluorenones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

An efficient method for construction of various fluorenones has been achieved via Rh(III)-catalyzed C–H activation/[4 + 2] annulation/aromatization sequences simple and readily available enaminones 1,3-dienes. This protocol showed good substrate compatibility as an array structurally electronically diverse prepared efficiently in moderate to yields preparative scale utility showing very efficiency the late-stage functionalization complex valuable molecules.

Language: Английский

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Rhodium-catalyzed site-selective cross-couplings of indoles and pyridotriazoles through carbene insertion

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110434 - 110434

Published: Sept. 1, 2024

Language: Английский

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Stereo- and Regioselective Installation of Vinyl Sulfonyl Fluoride onto Indoles without Transition-Metal Catalyst

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

Herein, we developed a practical method for synthesizing class of novel and highly valuable indolyl vinyl sulfonyl fluorides. This protocol has carved out path constructing broad range fluorinated indoles with exclusive stereo- regioselectivity through the Friedel-Crafts/elimination reaction without any transition-metal catalyst. transformation features mild conditions, high efficiency, excellent selectivity, rich substrate compatibility, highlighting its significant value in medicinal chemistry many related disciplines.

Language: Английский

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Insights into electrogenerated intermediates and rapid screening of electrochemical reactions by surface-modified carbon fiber paper redox spray ionization mass spectrometry

Analytica Chimica Acta, Journal Year: 2023, Volume and Issue: 1279, P. 341794 - 341794

Published: Sept. 7, 2023

Language: Английский

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Five-membered ring systems: pyrroles and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 199 - 250

Published: Jan. 1, 2023

Language: Английский

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Mn(I)‐Catalyzed C–H Allylation of Indoles with 2‐Vinylaziridines

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 8, 2024

Abstract Mn(CO) 5 Br‐catalyzed reaction of 1‐(2‐pyrimidyl)indoles with 1‐sulfonyl‐2‐vinylaziridines in THF the presence 0.25 equiv. NaOAc affords 2‐allylated indoles 31 % to 100 yields. The protocol suits for 3‐, 4‐, 5‐, 6‐, and 7‐substituted N‐(2‐pyrimidyl)pyrroles as well various 1‐(arylsulfonyl)‐2‐vinylaziridines such 1‐(phenylsulfonyl)‐2‐vinylaziridine, 1‐(naphthalen‐2‐ylsulfon‐yl)‐2‐vinylaziridine, 1‐(substituted phenylsulfonyl)‐2‐vinylazirid‐ines. Functional groups including alkyl, alkoxy, halogen, CHO, COOMe, CF 3 , CN, NO 2 are tolerated.

Language: Английский

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