Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5375 - 5379
Published: June 12, 2024
We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5375 - 5379
Published: June 12, 2024
We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between
Language: Английский
Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(22), P. 12313 - 12370
Published: Nov. 9, 2023
Late-stage functionalization (LSF) introduces functional group or structural modification at the final stage of synthesis natural products, drugs, and complex compounds. It is anticipated that late-stage would improve drug discovery's effectiveness efficiency hasten creation various chemical libraries. Consequently, products a productive technique to produce product derivatives, which significantly impacts biology development. Carbon-carbon bonds make up fundamental framework organic molecules. Compared with carbon-carbon bond construction, activation can directly enable molecular editing (deletion, insertion, atoms groups atoms) provide more efficient accurate synthetic strategy. However, selective unstrained still one most challenging projects in synthesis. This review encompasses strategies employed recent years for cleavage by explicitly focusing on their applicability functionalization. expands current discourse reactions providing comprehensive overview types bonds. includes C-C(sp), C-C(sp2), C-C(sp3) single bonds; double triple bonds, focus catalysis transition metals organocatalysts. Additionally, specific topics, such as ring-opening processes involving three-, four-, five-, six-membered rings, are discussed, exemplar applications these techniques showcased context bioactive molecules discovery. aims shed light advancements field propose potential avenues future research realm
Language: Английский
Citations
53Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 26, 2024
Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp
Language: Английский
Citations
24ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4287 - 4293
Published: Feb. 25, 2025
Language: Английский
Citations
3Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2093 - 2098
Published: March 11, 2022
Palladium-catalyzed synthesis of 3-acyl and -allyl indoles has been realized by merging nucleophilic cyclization ortho-alkynylanilines with ring opening three-membered rings such as cyclopropenones gem-difluorinated cyclopropanes. These functionalized were obtained in moderate to high yields stereoselectivity both cases. This protocol provides an alternative method toward under mild redox-neutral conditions.
Language: Английский
Citations
55ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(15), P. 8857 - 8867
Published: July 10, 2022
The unique properties of the fluorine-containing compounds and their widespread applications raise demand for dependable synthetic methods on precise introduction substituents into organic molecules. Herein, a site-divergent fluoroallylation olefins that can incorporate fluoroallyl motif different alkenyl C–H sites is disclosed. gem-Difluorinated cyclopropanes are employed as sources via rhodium-catalyzed C–C bond activation. This strategy provide two regioisomeric fluorinated skipped dienes in good yields with excellent site-selectivity. resulting products serve useful building blocks to access various molecules isosteric β, γ-unsaturated amides, which promising be exploited medicinal chemistry. Mechanistic studies revealed electronic property rhodium catalysts crucial controllable site-selectivity, providing more insights beyond methodology tuning selectivity metal catalysts.
Language: Английский
Citations
48ChemCatChem, Journal Year: 2022, Volume and Issue: 14(24)
Published: Aug. 11, 2022
Abstract gem ‐Difluorocyclopropanes (F 2 CPs) have aroused considerable attention not only from the structural perspective but also due to their ability participate in various valuable transformations. This Review summarizes advances catalytic ring‐opening reactions of ‐F CPs, especially emphasizing reactivities and applications those non‐activated ones under transition‐metal catalysis. Their achievements, synthetic limitations are discussed with aim stimulate enthusiasm for further development.
Language: Английский
Citations
48Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(23)
Published: April 4, 2023
Defluorinative manipulation of polyfluorinated molecules has shown great promise due to its granting synthetic versatility inert C-F bonds. The development chemo-, stereo- and regioselective strategies realize highly efficient formation either the linear/branched or E/Z products from gem-difluorocyclopropanes (gem-F2 CPs) is a challenging task. Herein, we have realized palladium/NHC-catalyzed fluoroallylation/annulation hydrazones with gem-F2 CPs that incorporate hydrazone N2 moiety into products. thermodynamically unstable fluorinated E-allylation aryl ketone were obtained for first time, while di-alkyl yielded monofluorinated branched selectivity under similar reaction conditions. With aldehyde hydrazones, two kinds pyrazoles via defluorinative allylation/annulation cascade, in which different carbon atoms could be incorporated pyrazole rings regiospecifically. DFT calculations revealed divergent was kinetically controlled final C-C bond proceeded through 7-membered TS.
Language: Английский
Citations
36Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(42)
Published: Aug. 12, 2023
Abstract An unprecedented Pd‐catalyzed fluorinative bifunctionalization of aziridines and azetidines was successfully developed via regioselective C−C C−F bond cleavage gem‐difluorocyclopropanes, leading to various β,β′‐bisfluorinated amines β,γ‐bisfluorinated amines. This reaction achieved by incorporating a 2‐fluorinated allyl group fluorine atom scissored from gem‐difluorocyclopropane in 100 % economy for the first time. The mechanistic investigations indicated that underwent amine attacking palladium complex generate η 2 ‐coordinated N‐allyl aziridine followed fluoride ligand transfer affording final β‐ γ‐fluorinated
Language: Английский
Citations
31Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3095 - 3102
Published: Jan. 1, 2023
A regiodivergent electrochemical defluorocarboxylation of gem -difluorocyclopropanes is realized, providing access to branched and linear carboxylated monofluorinated alkenes.
Language: Английский
Citations
30Green Chemistry, Journal Year: 2023, Volume and Issue: 25(17), P. 6733 - 6738
Published: Jan. 1, 2023
A metal free, visible-light driven α-C(sp 3 )−H gem-difluoroallylation of glycine derivatives with CF -alkenes and 1,3-enynes is presented under redox-neutral conditions good yields excellent functional group compatibility.
Language: Английский
Citations
29