Organophotoredox-Catalyzed C(sp²)–H Difluoromethylenephosphonation of Imidazoheterocycles

Organic Letters, Journal Year: 2019, Volume and Issue: 21(14), P. 5606 - 5610

Published: July 8, 2019

A mild and efficient method for the direct difluoromethylenephosphonation of imidazopyridines has been developed using rose bengal (RB) as a photoredox catalyst. Bis(pinacolato)diboron (B2pin2) is found to be crucial additive in present reaction. The methodology also applicable other heterocycles like imidazo[2,1-b]thiazole, benzo[d]imidazo-[2,1-b]thiazole, indole. reaction possibly proceeds through single electron transfer (SET) process.

Language: Английский

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Late‐Stage ¹⁸ F‐Difluoromethyl Labeling of N‐Heteroaromatics with High Molar Activity for PET Imaging

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(37), P. 13149 - 13154

Published: July 19, 2019

Despite a growing interest in CHF2 medicinal chemistry, there is lack of efficient methods for the insertion CHF18 F into druglike compounds. Herein described photoredox flow reaction 18 F-difluoromethylation N-heteroaromatics that are widely used chemistry. Following two-step synthesis new reagent, completed within two minutes and proceeds by C-H activation, circumventing need pre-functionalization substrate. The method operationally simple affords straightforward access to radiolabeled with high molar activity suitable biological vivo studies clinical application.

Language: Английский

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Synthesis of Monofluoroalkenes through Visible-Light-Promoted Defluorinative Alkylation of gem-Difluoroalkenes with 4-Alkyl-1,4-dihydropyridines

Organic Letters, Journal Year: 2020, Volume and Issue: 22(4), P. 1542 - 1546

Published: Jan. 28, 2020

In this study, a facile and efficient method to synthesize monofluoroalkenes by photoredox catalytic defluorinative alkylation of gem-difluoroalkenes with 4-alkyl-1,4-dihydropyridines under mild conditions (room temperature) is described. This novel strategy applicable for broad range gem-difluoroalkene substrates good functional group tolerance variety (including primary, secondary, even tertiary alkyl radicals). Moreover, it also allows the challenging radical coupling glycosyl-based (DHPs) monofluoroalkenylated saccharides.

Language: Английский

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Transition‐Metal‐Catalyzed Monofluoroalkylation: Strategies for the Synthesis of Alkyl Fluorides by C−C Bond Formation

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(7)

Published: Oct. 20, 2021

Abstract Alkyl fluorides modulate the conformation, lipophilicity, metabolic stability, and pKa of compounds containing aliphatic motifs and, therefore, have been valuable for medicinal chemistry. Despite significant research in organofluorine chemistry, synthesis alkyl fluorides, especially chiral remains a challenge. Most commonly, are prepared by formation C−F bonds (fluorination), numerous strategies nucleophilic, electrophilic, radical fluorination reported recent years. Although to access C−C bond (monofluoroalkylation) inherently convergent complexity‐generating, they studied less than methods based on fluorination. This Review provides an overview developments (enantioenriched or racemic) secondary tertiary monofluoroalkylation catalyzed transition‐metal complexes. We expect this contribution will illuminate potential monofluoroalkylations simplify complex suggest further directions growing field.

Language: Английский

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Hydrogenation of fluorinated molecules: an overview

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(14), P. 8178 - 8192

Published: Jan. 1, 2021

The review aims at providing an overview on the developments made in hydrogenation reactions of molecules having various fluorinated groups (F, CF₃, CF₂H, CF₂R_f).

Language: Английский

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