Transition-Metal-Free Late-Stage Decarboxylative gem-Difluoroallylation of Primary Alkyl Acids

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15234 - 15247

Published: Oct. 8, 2024

A transition-metal-free late-stage decarboxylative gem-difluoroallylation of carboxylic acids with α-trifluoromethyl alkenes has been described by the use organo-photoredox catalysis. Both primary alkyl and heteroaryl were readily incorporated. This approach merits feedstock materials, mild reaction conditions, wide functionality tolerance. The synthetic utility this highlighted functionalization a variety acid-containing natural products drug molecules.

Language: Английский

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Sequential Photocatalysis for Homologative Diversification of α-Amino Acids to β-Amino Acids Via Phosphonium Ylide Linchpin Strategy

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

β-Amino acids serve as crucial building blocks for a broad range of biologically active molecules and peptides with potential peptidomimetics. While numerous methods have been developed the synthesis β-amino acids, most them require multistep preparation specific reagents substrates, which limits their synthetic practicality. In this regard, homologative transformation abundant readily available α-amino would be an attractive approach acid synthesis. Herein, we disclose development sequential process to provide diverse from derivatives commercially phosphonium ylides via visible light photoredox catalysis. two-step protocol, function bifunctional linchpin: they act carbon nucleophile forge C-C bond in first step carbon-centered radical source modifications scaffold second step. The orthogonal activation these reactivities under mild photocatalytic conditions enables modular three-component assembly access dipeptides high structural diversity.

Language: Английский

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Photoredox Catalyzed Synthesis of gem-Difluoroalkenes and Monofluorinated Cyclooctenes via 1,5-HAT Process

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4548 - 4553

Published: May 17, 2024

gem-Difluoroalkenes and monofluorinated cycloalkenes have emerged as basic structural units in a variety of bioactive molecules natural products. Thus, developing straightforward efficient methods for synthesizing fluorinated alkene compounds is considerable significance. Herein, we disclose visible-light-induced defluorination 2-trifluoromethyl-1-alkene via 1,5-HAT process using N-alkoxyphtalimides both radical precursor potential nucleophile. The mild stepwise reaction leads to structurally diverse gem-difluoroalkenes cyclooctenes with high efficiency, respectively.

Language: Английский

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Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8342 - 8356

Published: May 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Language: Английский

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Chemodivergent alkylation of trifluoromethyl alkenes via photocatalytic coupling with alkanes

Green Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A photocatalytic methodology for the chemodivergent direct cross-coupling of simple alkanes with trifluoromethyl alkenes that enables selective formation gem -difluoroalkenes and is presented.

Language: Английский

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