Reaction Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 7(6), P. 1247 - 1275
Published: Jan. 1, 2022
Aryl diazonium salts play an important role in chemical transformations; however their explosive nature limits applications batch.
Language: Английский
Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2752 - 2906
Published: Aug. 10, 2021
Photoinduced chemical transformations have received in recent years a tremendous amount of attention, providing plethora opportunities to synthetic organic chemists. However, performing photochemical transformation can be quite challenge because various issues related the delivery photons. These challenges barred widespread adoption steps industry. past decade, several technological innovations led more reproducible, selective, and scalable photoinduced reactions. Herein, we provide comprehensive overview these exciting advances, including flow chemistry, high-throughput experimentation, reactor design scale-up, combination photo- electro-chemistry.
Language: Английский
Citations
536
Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(8), P. 4237 - 4352
Published: Jan. 24, 2023
The emergence of modern photocatalysis, characterized by mildness and selectivity, has significantly spurred innovative late-stage C–H functionalization approaches that make use low energy photons as a controllable source. Compared to traditional strategies, photocatalysis paves the way toward complementary and/or previously unattainable regio- chemoselectivities. Merging compelling benefits with workflow offers potentially unmatched arsenal tackle drug development campaigns beyond. This Review highlights photocatalytic strategies small-molecule drugs, agrochemicals, natural products, classified according targeted bond newly formed one. Emphasis is devoted identifying, describing, comparing main mechanistic scenarios. draws critical comparison between established ionic chemistry photocatalyzed radical-based manifolds. aims establish current state-of-the-art illustrate key unsolved challenges be addressed in future. authors aim introduce general readership functionalization, specialist practitioners evaluation methodologies, potential for improvement, future uncharted directions.
Language: Английский
Citations
322
Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(4), P. 1798 - 1816
Published: Sept. 27, 2021
Language: Английский
Citations
134
Chemical Science, Journal Year: 2022, Volume and Issue: 13(19), P. 5659 - 5666
Published: Jan. 1, 2022
General photoactivation of EDA complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2.2]octane was discovered. This practical mode enables the generation aryl radicals for C–H functionalization arenes.
Language: Английский
Citations
126
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(18), P. 10431 - 10440
Published: April 26, 2023
Great success in synthetic chemistry is motivated by the development of novel and reactive linchpins for carbon-carbon carbon-heteroatom bond formation reactions, which has dramatically altered chemists' approach to building molecules. Herein, we report ready synthesis aryl sulfonium salts, a versatile electrophilic linchpin, via Cu-mediated thianthrenation phenoxathiination commercially available arylborons with thianthrene phenoxathiine, providing series salts high efficiency. More importantly, leveraging sequential Ir-catalyzed C-H borylation arylborons, formal arenes also achieved. The undirected normally occurred at less steric hindrance position, thus complementary method comparison thianthrenation. This process capable late-stage functionalization pharmaceuticals, might find wide applications both industry academic sectors.
Language: Английский
Citations
53
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(10), P. 1538 - 1564
Published: March 6, 2023
Abstract Quaternary pyridinium compounds are valuable intermediates in organic synthesis, which have gained immense popularity the synthetic community. The application of transition metal or photoredox catalysis transforming quaternary into various C−C and C−X bonds is well established. A majority these methods require high temperatures, expansive catalysts, delicate conditions for successful execution. On other hand, use metal‐free photocatalysis‐free strategies constructing using derivatives has been sought‐after. In this context, electron‐donor‐acceptor (EDA)‐complex reactions emerged as a state‐of‐the‐art methodology, do not any photocatalyst their EDA‐complex photochemistry takes advantage electron‐acceptor ability derivatives, can quickly generate radical precursor via deaminative process. These newly generated useful several transformations. We hereby, review, discuss an area major progress mediated involving with mechanism, substrate scope, limitations. magnified image
Language: Английский
Citations
43
Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 529, P. 216438 - 216438
Published: Jan. 17, 2025
Language: Английский
Citations
2
Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(52), P. 27070 - 27077
Published: Oct. 15, 2021
Abstract The engagement of unactivated alkyl halides in copper‐catalyzed cross‐coupling reactions has been historically challenging, due to their low reduction potential and the slow oxidative addition copper(I) catalysts. In this work, we report a novel strategy that leverages halogen abstraction ability aryl radicals, thereby engaging diverse range iodides Negishi‐type at room temperature. Specifically, radicals generated via copper catalysis efficiently initiate cleavage carbon–iodide bonds iodides. thus enter catalytic cycles couple with difluoromethyl zinc reagent, furnishing difluoromethane products. This unprecedented difluoromethylation approach applied late‐stage modification densely functionalized pharmaceutical agents natural
Language: Английский
Citations
56
Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(4), P. 1622 - 1633
Published: Jan. 21, 2022
Naturally occurring hydrazones are rare despite the ubiquitous usage of synthetic in preparation organic compounds and functional materials. In this study, we discovered a family novel microbial metabolites (tasikamides) that share unique cyclic pentapeptide scaffold. Surprisingly, tasikamides A–C (1–3) contain hydrazone group (C═N─N) joins peptide scaffold to an alkyl 5-hydroxylanthranilate (AHA) moiety. We biosynthesis 1–3 requires two discrete gene clusters, with one encoding nonribosomal synthetase (NRPS) pathway for assembling another AHA-synthesizing pathway. The AHA cluster encodes three ancillary enzymes catalyze diazotization yield aryl diazonium species (diazo-AHA). electrophilic diazo-AHA undergoes nonenzymatic Japp–Klingemann coupling β-keto aldehyde-containing precursor furnish 1–3. studies together unraveled mechanism whereby specialized formed by biosynthetic pathways via unprecedented vivo reaction. findings raise prospect exploiting arylamine-diazotizing (AAD) synthesis modification biological macromolecules.
Language: Английский
Citations
46
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(47)
Published: Sept. 7, 2022
Herein, we report a photocatalyzed Meerwein-type bromoarylation of alkenes with stable arylthianthrenium salts, formed by site-selective C-H thianthrenation. This protocol can be applied to late-stage functionalization variety biomolecules that are difficult access other aryl coupling reagents. Halogen introduction allows for follow-up transformations, affording numerous biologically active skeletons.
Language: Английский
Citations
43