Site‐Specific Synthesis of β‐Fluorinated γ‐Butyrolactams via Decarboxylative Fluorination of β‐Carboxyl‐γ‐Butyrolactams

Phae-nok, Supasorn; Pohmakotr, Manat; Kuhakarn, Chutima; Reutrakul, Vichai; Soorukram, Darunee

doi:10.1002/ejoc.201900685

Cited by 13 publications

(5 citation statements)

References 103 publications

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“…Their protocol employs Selectfluor as a fluorine source in the presence of trifluoroacetic acid. A related protocol using stoichiometric amount of AgNO 3 was employed in the synthesis of β‐fluorinated γ‐butyrolactones and ‐lactams [215,216] . The use of 5‐substituted lactones and lactams led to a mixture of diastereomeric fluorides, with diastereomeric ratios (d.r.)…”

Section: Decarboxylative C‐halogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

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Section: Decarboxylative C‐halogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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“…Similar results were also observed for other cyclic hexyl carboxylic acid substrates (8, 9), while carboxylic acids bearing dihydroindene (10) and tetrahydronaphthalene (11) led to lower yields due to volatilization loss, while a structurally similar linear substrate (12) resulted in 66% yield of product. Notably, the product βfluoro-γ-butyrolactam 13, which was previously produced with a stoichiometric Ag salt, 18 could be prepared smoothly using a catalytic amount of iron salt. The reaction enjoyed good functional group tolerance with the case of phosphine oxide as an interesting example (14).…”

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confidence: 99%

Visible-Light-Induced Decarboxylative Fluorination of Aliphatic Carboxylic Acids Catalyzed by Iron

et al. 2022

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An efficient and inexpensive protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids catalyzed with iron salts under visible light is presented. This new method allows the facile fluorination of a diverse array of carboxylic acids even on gram scale using a Schlenk flask without loss of efficiency. Mechanistic studies suggest that the photoinduced ligand-to-metal charge transfer process enables the generation of the key step to generate the carboxyl radical intermediates.

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“…[ 85 ] For example, β−selective fluorination of pyrrolidines could be achieved with decarboxylative fluorination of the corresponding carboxylic acids (Scheme 27). [ 86 ] Notably, 1,5‐hydrogen transfer was observed with n‐butyl substituted β‐carboxyl‐pyrrolidines, producing remote fluorinated products in addition to the decarboxylative fluorinated ones.…”

Section: Electrophilic Fluorination Reagentsmentioning

confidence: 99%

Recent Advances in C—F Bond Formation from Carbon‐Centered Radicals

Zhang,

Wang,

Cheng

2024

Chin. J. Chem.

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Comprehensive SummaryConstruction of C–F bonds is a direct and efficient method for introducing fluorine into pharmaceuticals, agrochemicals, and materials. Strategies such as nucleophilic, electrophilic, radical, and transition‐metal catalyzed fluorination have been developed to meet the demand of diverse C–F bond formation. Among them, radical fluorination has been witnessed with substantial advancement in a recent decade. Herein, we reviewed methods for formation of C–F bonds with carbon‐centered radicals as key intermediates, especially in recent five years. We introduce in the paper with different fluorinating reagents, strategies for radical generation, and application in late‐stage functionalization and synthesis of PET tracers. We also indicate the current limitations and propose the direction of the field for the future development.This article is protected by copyright. All rights reserved.

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Site‐Specific Synthesis of β‐Fluorinated γ‐Butyrolactams via Decarboxylative Fluorination of β‐Carboxyl‐γ‐Butyrolactams

Cited by 13 publications

References 103 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Visible-Light-Induced Decarboxylative Fluorination of Aliphatic Carboxylic Acids Catalyzed by Iron

Recent Advances in C—F Bond Formation from Carbon‐Centered Radicals

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