Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9085 - 9090
Published: Oct. 16, 2024
A novel and efficient modular synthesis of
Language: Английский
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(32), P. 17527 - 17550
Published: Aug. 2, 2023
The C–O bond is ubiquitous in biologically active molecules, pharmaceutical agents, and functional materials, thereby making it an important group. Consequently, the development of bond-forming reactions using catalytic strategies has become increasingly research topic organic synthesis because more conventional methods involving strong base acid have many limitations. In contrast to ionic-pathway-based methods, copper-promoted radical-mediated formation experiencing a surge interest owing renaissance free-radical chemistry photoredox catalysis. This Perspective highlights appraises state-of-the-art techniques this burgeoning field. contents are organized according different reaction types working models.
Language: Английский
Citations
40
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(14), P. 10167 - 10176
Published: March 27, 2024
The π-bond enrichment frameworks not only serve as a crucial building block in organic synthesis but also assume pivotal role the fields of materials science, biomedicine, photochemistry, and other related disciplines owing to their distinctive structural characteristics. incorporation various substituents into C═C double bonds tetrasubstituted alkenes is currently highly significant research area. However, with diverse on poses challenge achieving stereoselectivity. Here, we reported an efficient convergent route Cu-catalyzed borylalkynylation both symmetrical unsymmetrical 1,3-diynes, B2pin2, acetylene bromide construction boronated phenyldiethynylethylene (BPDEE) derivatives excellent chemo-, stereo-, regioselectivities. BPDEE could transform novel π-conjugated gem-diphenyldiethynylethylene (DPDEE), vinylphenyldiethynylethylene (VPDEE), phenyltriethynylethylene (PTEE) by stepwise process, which provides flexible platform for complex that were difficult synthesize previous methods. initial optical characterization revealed synthesized molecules exhibited aggregation-induced emission (AIE) properties, further establishes groundwork future applications enriches advances field functional research.
Language: Английский
Citations
15
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13279 - 13290
Published: Aug. 31, 2023
A strategy utilizing silver-catalyzed oxidative decarboxylation radical cascade cyclization of arylthiodifluoroacetic acids with alkenes for the simple and efficient preparation difluoromethylated thiochromanes 2,2-disubstituted-N-arylbutanamides derivatives has been developed. This approach includes good functional group tolerance, easily accessible starting materials, operational simplicity.
Language: Английский
Citations
16
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 16, 2025
A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: March 28, 2025
Vinyl difluoromethylene units (−CF−) significantly enhance the bioactivity and physical chemical properties of compounds. Despite recent advances in introducing vinyl units, radical-mediated formation these motifs remains largely unexplored. A novel serial catalytic strategy for selective defluoroalkylation trifluoromethyl alkenes has been developed, utilizing photocatalytic defluorocarboxylation followed by photoinduced iron-catalyzed decarboxylation/isomerization. The reaction involves generating difluoroallyl radicals, tautomerizing to proceeding through radical addition alkylation.
Language: Английский
Citations
0
Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(21), P. 2819 - 2824
Published: June 25, 2023
Comprehensive Summary Due to its unique electronic properties, the difluoromethylene group (CF 2 ) has served as a valuable unity in design of biologically active molecules. Since γ‐lactones display broad range biological α,α‐difluoro‐γ‐lactones may exhibit unexpected activities, and thus their synthesis received increasing attention. Traditional synthetic methods suffer from tedious multi‐ step processes, very few effective have been reported recently. Herein, we describe difunctionalization alkenes with BrCF CO K under photoredox catalysis use boron‐Lewis acid for access α,α‐difluoro‐γ‐lactones. In this transformation, alkene substrates used reagents, including acid, PhB(OH) or BF 3 ·THF, are cheap widely available. High efficiency atom economy make protocol attractive.
Language: Английский
Citations
9
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3717 - 3723
Published: Jan. 1, 2024
Visible-light-induced phosphine-catalyzed radical cyclization of bromodifluoroacyl arenes with diverse alkenes, affording a variety cyclic gem -difluoroacyl scaffolds in good to excellent yields.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13457 - 13471
Published: Sept. 3, 2024
Organic molecules containing a difluoroalkyl group are valuable and versatile chemicals because of their unique physicochemical biological properties. Accordingly, the development efficient practical difluoroalkylation for preparation these compounds is important attractive. Herein, we demonstrate photoredox-catalyzed base-dependent selective carbodifluoroalkylation halodifluoroalkylation alkenes using readily available 2-(allyloxy)arylaldehydes [or 2-(allylamino)arylaldehydes] XCF
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 30, 2024
Herein, we report a visible light-induced difluoromethylation cyclization and subsequent amination-defluorination reaction. This protocol allows efficient to valuable 3-fluoro-quinolinones in moderate excellent yields. A sequential difluoromethylation-cyclization-amination-defluorination mechanism was proposed based on study. Further density functional theory (DFT) calculations revealed that the base K
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5619 - 5633
Published: April 5, 2024
Hydroxanthones have attracted considerable attention due to their significance in organic and biological chemistry, yet synthesis remains a great challenge. In this study, series of chromone-tethered alkenes are designed, radical cyclization reaction these chromone derivatives has been achieved under photoredox conditions. The uses bromodifluoroacetamides or bromodifluoroacetates as coupling partners, affording broad range functionalized tetrahydroxanthone products with up 85% yields. is triggered via the generation difluoroacetate radicals alkene cations fac-Ir(ppy)3 2,3,5,6-tetrakis(carbazol-9-yl)-1,4-dicyanobenzene photocatalyst. This approach offers access various from readily available starting materials enriches research content heteroarene-tethered alkenes.
Language: Английский
Citations
1