Metal-Free Synthesis of Trifluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines via Dehydrative Coupling of Imidazo[1,2-a]pyridines with Trifluoroacetaldehyde

Synthesis, Journal Year: 2024, Volume and Issue: 56(11), P. 1756 - 1764

Published: Jan. 25, 2024

Abstract A facile and efficient method for the synthesis of trifluoromethylated carbinols has been developed from imidazo[1,2-a]pyridines trifluoroacetaldehyde. The direct C(sp2)–H hydroxytrifluoromethylation is successfully implemented at room temperature using HFIP as solvent through dehydrative cross-coupling process, which displays a broad substrate scope functional group tolerance. Furthermore, gram-scale synthetic transformation experiments have also demonstrated, indicate its potential applicable values in organic synthesis. This green protocol features operational simplicity, atom economy, mild reaction conditions (e.g., temperature, transition-metal- oxidant-free, without inert gas protection), wide scope, excellent practicality.

Language: Английский

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Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones

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

Published: April 22, 2025

A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported N-trifluoroethylaminopyridinium salt was achieved in the absence transition metal catalysts or bases. Notable features this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that reaction proceeds via radical pathway, involving an situ generated N-trifluoroethyl radical, followed by 1,2-H shift.

Language: Английский

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Total Synthesis of Alanense A through an Intramolecular Friedel–Crafts Alkylation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 2050 - 2054

Published: Jan. 19, 2024

The first total synthesis of cadinane sesquiterpenoid alanense A, in which an intramolecular dehydrative Friedel–Crafts alkylation 2,5-diaryl-2-pentanol is incorporated as a key step, has been achieved. combinatorial use p-TsOH·H2O catalyst and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) solvent provides 1,1-disubstituted tetrahydronaphthalene 97% yield. It was also found that the combination p-TsOH HFIP effective for removal phenolic MOM ether.

Language: Английский

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HFIP-promoted synthesis of imidazo [1,2-a]pyridines containing CF3-substituted tertiary alcohols at room temperature

Tetrahedron, Journal Year: 2024, Volume and Issue: 156, P. 133943 - 133943

Published: March 19, 2024

Language: Английский

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Electrochemical-induced solvent-tuned selective C(sp³)–H bond activation towards the synthesis of C3-functionalized chromone derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(38), P. 5050 - 5053

Published: Jan. 1, 2024

An unprecedented solvent-tuned electrochemical method for selective C(sp

Language: Английский

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An update on the advances in chromone and the derivatives synthesis based on the key chromone annulation of o-hydroxyaryl enaminones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110784 - 110784

Published: Dec. 1, 2024

Language: Английский

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C3-Alkylation of Imidazo[1,2-a]pyridines via Three-Component Aza-Friedel–Crafts Reaction Catalyzed by Y(OTf)3

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3463 - 3463

Published: July 24, 2024

As an important class of nitrogen-containing fused heterocyclic compounds, imidazo[1,2-a]pyridines often exhibit significant biological activities, such as analgesic, anticancer, antiosteoporosis, anxiolytic, etc. Using Y(OTf)

Language: Английский

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Catalytic Enantioselective Aldol Reactions of Pyruvates as Nucleophiles with Chlorinated and Fluorinated Aldehydes and Ketones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15972 - 15978

Published: Oct. 23, 2024

Reactions of pyruvates as nucleophiles under catalytic conditions are difficult to control without the use enzymes catalysts. Here, enantioselective aldol reactions with chlorinated and fluorinated aldehydes ketones organocatalytic conditions, in which act nucleophiles, reported. Based on analyses self-aldol presence model catalysts, catalysts desired cross were developed. Using primary amine-derived catalyst, products, i.e., γ-chlorinated alkyl or γ-fluorinated group-substituted γ-hydroxy α-ketoesters, obtained good high yields enantioselectivities.

Language: Английский

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HFIP promoted cyclization of o-hydroxyaryl enaminones with chlorohydrocarbon for synthesis of chromone-containing triarylmethanes

Tetrahedron, Journal Year: 2024, Volume and Issue: 156, P. 133948 - 133948

Published: March 16, 2024

Language: Английский

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Brønsted Acid Catalyzed Dehydroxylative Cyanation of Benzylic Alcohols with Trimethylsilyl Cyanide Using 1,1,1,3,3,3‐Hexafluoro‐2‐propanol as a Solvent

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: May 7, 2024

Abstract A concise and direct Brønsted acid catalyzed cyanation of secondary tertiary benzylic allylic alcohols has been developed using trimethylsilyl cyanide (TMSCN) as a source 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) solvent. The present transition‐metal‐free catalytic process is operationally simple to perform under “open‐flask” conditions applicable the preparation number α‐arylacetonitriles well late‐stage material transformations. effectiveness protocol was further demonstrated by first enantioselective synthesis determination absolute configuration verimol F.

Language: Английский

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