C3 versus C5 Regioselectivity in the Intramolecular Dehydrative Friedel–Crafts Alkylation of Indole C4-Tethered Carbinols

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 3, 2025

Described herein is a mild catalytic dehydrative Friedel-Crafts alkylation of 1,1-diarylalkanols─a challenging reaction with exceedingly rare previous success, presumably because the unfavorable steric hindrance around reactive centers and competitive E1 reaction. Executing in an intramolecular fashion benefiting from high nucleophilicity indole, we have successfully utilized this synthesizing 3,4-fused indoles. Interestingly, strategy could also be applied to access 4,5-fused indoles via modification tether connecting alcohol indole moieties.

Language: Английский

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Effect of sustainable and confined media on the photoinduced [6π]‐electrocyclization reaction of diphenyl and N‐methyldiphenylamines

ChemPhotoChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 22, 2024

Abstract A systematic investigation of the photoinduced [6π]‐electrocyclization reaction diphenylamine and N‐methyldiphenylamine has been carried out under steady‐state time‐resolved conditions in homogeneous (cyclohexane, acetonitrile methanol) micellar solutions (sodium dodecyl sulfate ‐SDS, cetyltrimethylammonium chloride‐CTAC polyethylene glycol monododecyl ether‐Brij P35). The photolysis such compounds both micro‐heterogeneous media afforded corresponding carbazoles almost quantitative yield oxidative conditions. Furthermore, relative rate formation photoproducts increases when moving from to solution, due environmental confined hydrophobic core as highlighted by 1D 2D NMR (NOESY DOSY) spectroscopic analyses.

Language: Английский

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Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5589 - 5605

Published: April 5, 2024

Diversity-oriented synthesis strategy for the efficient assembly of indole-fused polycyclic scaffolds via rhodium-catalyzed NH-indole-directed C–H coupling with propargylic alcohol derivatives in a regioselective manner was developed. Five 2-phenyl-1H-indole-embedded core skeletons were synthesized. In particular, three different exo-olefin-containing polycycles realized, which may be manipulated further chemistry.

Language: Английский

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Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7285 - 7290

Published: Aug. 23, 2024

We have disclosed silver(I)-induced switching of regioselectivity in rhodium-catalyzed C–H alkynylation indole derivatives with the help a pivaloyl directing group by tuning metalation modes. The judicious choice AgOAc, Ag2O, and Ag2CO3 affords an array C2-alkynylated indoles, C4-alkynylated C2,C4-dialkynylated respectively. synthetic utility alkyne fragment is demonstrated derivatization into valuable indole-based compounds.

Language: Английский

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Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(8)

Published: Nov. 30, 2023

Carbazole is a heterocyclic motif that can be found in diverse array of natural and unnatural products displaying wide range biological physiological properties. Furthermore, this heterocycle part electronic materials like photoconducting polymers organic optoelectronic owing to its excellent photophysical characteristics. Consequently, the development synthetic strategies for carbazole scaffolds holds potential significance material fields. In regard, variety preparation methods has been developed exploit their efficient distinct formation new C-C C-heteroatom bonds under mild conditions enabling broad substrate diversity functional group tolerance. Therefore, review focuses on synthesis set derivatives describing methodologies involve direct irradiation, photosensitization, photoredox, electrochemical thermal cyclization reactions.

Language: Английский

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Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐heterocycles with N‐methoxyindoleamides and Isoxazolones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4089 - 4094

Published: July 20, 2024

Abstract A method for synthesizing pyrimido[ 1,2‐a ]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C−H activation/annulation strategy employing N ‐methoxyindoleamides and isoxazolones is developed. Also, framework of 3‐methoxy‐2,3‐dihydro‐[ 1,3,5 ]triazino[ ]indole‐4,10‐dione was successfully synthesized Cp*Rh‐catalyzed activation/annulation/oxidation reaction between N‐ (methyloxy)‐1 H ‐indole‐1‐carboxamide isoxazolones. These reactions demonstrated the suitability several substrates, compatibility with numerous functional groups, mild conditions. Preliminary mechanistic investigations have been completed.

Language: Английский

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Synthesis of indol-3-yl-benzofurans and carbazoles via Cu(OTf)₂-catalyzed [3 + 2] and [4 + 2] cycloaddition

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(33), P. 6690 - 6694

Published: Jan. 1, 2024

An efficient Cu(OTf)

Language: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

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