Pd-Catalyzed Divergent Site-Selective Difluoromethylation and Difluoromethylcarbonylation of Aryl Sulfonium Salts

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(18), P. 13557 - 13566

Published: Aug. 28, 2024

The incorporation of the difluoromethyl (CF2H) group into arenes has increasingly been recognized as important in drug discovery. Herein, we report a divergent cross-coupling method for constructing both aryl difluoromethanes and difluoroketones from thianthrenium salts. Site selectivity Negishi-type coupling C1 insertion reactions was achieved under palladium catalysis. Both transformations proceed with broad functional tolerance, enabling late-stage difluoromethylation difluoromethylcarbonylation complex molecules. synthetic utility this demonstrated by synthesizing four pharmaceutical analogues same precursor applying it downstream functionalization difluoroketones.

Language: Английский

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Expanding tracer space for positron emission tomography with high molar activity 18F-labeled α,α-difluoromethylalkanes

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 13, 2025

Abstract Positron emission tomography (PET) is an advanced biomedical imaging modality that relies on well-designed radiotracers to report specific protein targets and processes occurring in living animals humans. Cyclotron-produced short-lived fluorine-18 ( t 1/2 = 109.8 min) widely used radiolabel tracers for PET. Herein we aim expand the chemical space available PET tracer development include structures with 18 F-labeled α,α-difluoromethylalkyl groups. We efficient broad-scope method labeling such groups high molar activities based a single-step radiofluorination of α-bromo-α-fluoroalkanes. The applicable bioactive compounds drug-like molecules, readily automated radiotracer production. unique physical biochemical features α,α-difluoromethyl group can now be exploited design new tracers.

Language: Английский

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Research Progress on Palladium-Catalyzed Difluoromethyl Arylation

Journal of Organic Chemistry Research, Journal Year: 2025, Volume and Issue: 13(01), P. 21 - 34

Published: Jan. 1, 2025

Language: Английский

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Palladium-Catalyzed Trifluoroacetylation of Arylboronic Acids Using a Trifluoroacetylation Reagent

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7233 - 7238

Published: Aug. 19, 2024

A new trifluoroacetylation reagent was developed by using inexpensive and readily available trifluoroacetic anhydride N-phenyl-4-methylbenzenesulfonamide for the first time. The reaction of (het)aryl boronic acids with reagent, N-phenyl-N-tosyltrifluoroacetamide, proceeded smoothly in presence a palladium catalyst to provide trifluoromethyl ketones satisfactory excellent yields. Various groups, including synthetically useful functional groups Cl, TMS, PhCO, were tolerated well under current conditions. This can be used large-scale synthesis ketones, even at low loading.

Language: Английский

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Site-Specific Dehydrogenative Hydroxyfluoroalkylation of Indoles with Hexafluoroisopropanol

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

Published: Nov. 22, 2024

An efficient and convenient method for the synthesis of C3-hydroxytrifluoroalkylated indoles pyrroles was described in this paper. The copper-catalyst-free site-specific cross-dehydrogenative coupling reaction various with hexafluoroisopropanol proceeded smoothly by using MnO

Language: Английский

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