ChemInform Abstract: Silver‐Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to β‐Fluorinated γ‐Butyrolactones.

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

doi:10.1002/chin.201536123

Cited by 2 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[24] Since then, the AgNO 3 mediated fluorination with selectfluor becomes a general method to construct C(sp 3 )-F bond. [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: C-halide Fluorinationmentioning

confidence: 99%

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

Zhang,

Wang,

Cheng

2024

Chin. J. Chem.

View full text Add to dashboard Cite

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.

show abstract

Section: C-halide Fluorinationmentioning

confidence: 99%

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

Zhang,

Wang,

Cheng

2024

Chin. J. Chem.

View full text Add to dashboard Cite

show abstract

“…To begin with, the decarboxylation was examined by using 1a as a model substrate. Initially, treatment of 1a with AgNO 3 (1 equiv) and K 2 S 2 O 8 (1 equiv) in refluxing dry MeCN (open flask) for five hours gave the desired β-nitro γ-butyrolactone 2a in 28% yield, along with the β-hydroxy γ-butyrolactone 3a in 26% yield and the α,β-unsaturated γ-butyrolactone 4a 7b in 5% yield (Table1, entry 1). Compounds 2a , 3a , and 4a could be readily isolated by flash column chromatography on silica gel.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Phae-nok¹,

Kuhakarn²,

Leowanawat³

et al. 2022

Synlett

Self Cite

View full text Add to dashboard Cite

Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β position as their characteristic functionality, using a combination of AgNO3/K2S2O8 was investigated. The dual function of AgNO3 as an initiator for decarboxylation process and a nitrogen dioxide radical source that reacts with aliphatic carboxylic substrates of this study was reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41-85% yields) with moderate selectivity in one-pot operation. The reactions completed within acceptable reaction time (2 h) under mild reaction conditions that γ-butyrolactone core could be tolerated. The present study represents the direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones which are important precursors in organic transformations.

show abstract

ChemInform Abstract: Silver‐Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to β‐Fluorinated γ‐Butyrolactones.

Abstract: Silver-Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to -Fluorinated -Butyrolactones. -(PHAE-NOK, S.; SOORUKRAM*, D.; KUHAKARN, C.; REUTRAKUL, V.; POHMAKOTR, M.; Eur. J. Org. Chem. 2015, 13, 2879-2888, http://dx.

Cited by 2 publications

References 1 publication

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

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

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Contact Info

Product

Resources

About