Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Herein, we report an unprecedented oxidative decarboxylative C–O cross-coupling reaction for the esterification of feedstock α-keto carboxylic acids and alcohols under mild conditions.
Language: Английский
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)
Published: Jan. 20, 2024
Abstract A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, does not require oxidizing agents. It exhibits wide substrate compatibility can be easily scaled up to gram scale.
Language: Английский
Citations
9
Green Chemistry, Journal Year: 2024, Volume and Issue: 26(4), P. 2241 - 2247
Published: Jan. 1, 2024
A water-soluble type II photosensitizer with excellent water solubility was utilized for selective photooxidation reactions of hydroazaobenzenes, olefins, and hydrosilanes in water.
Language: Английский
Citations
8
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(29)
Published: May 16, 2024
Abstract Transition metal‐catalyzed carbene transfer reactions have a century‐old history in organic chemistry and are primary method for the synthesis of cyclopropanes. Much work this field has focused on use diazo compounds related precursors, which can fragment to catalyst with concomitant loss stable byproduct. Despite utility approach, there persistent limitations scope viable carbenes, most notably those lacking stabilizing substituents. By coupling two‐electron redox cycles, it is possible expand available starting materials that be used as precursors. In Minireview, we discuss emerging catalytic reductive cyclopropanation using either gem ‐dihaloalkanes or carbonyl compounds. This strategy inspired by classic stoichiometric transformations, such Simmons–Smith Clemmensen reduction, but instead entails formation catalytically generated transition metal carbenoid. We also present recent efforts generate carbenes directly from methylene (CR 2 H ) groups via formal 1,1‐dehydrogenation. These currently restricted substrates containing electron‐withdrawing substituents, serve facilitate deprotonation subsequent oxidation anion.
Language: Английский
Citations
8
Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(9), P. 957 - 962
Published: Jan. 18, 2024
Comprehensive Summary Multicomponent alkene 1,2‐dicarbofunctionalizations (DCFs) have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C—C double bond in step for enhancing molecular complexity and diversity. To the best of our knowledge, there is only report on photoredox‐catalyzed three‐component DCFs with malonates through radical−radical cross‐coupling, while radical‐polar crossover (RPC)‐type were still rare. Herein, we describe redox‐neutral RPC‐type 1,2‐dialkylation styrenes aldehydes synergistic Brønsted base/photoredox catalysis system. This transition‐metal‐free provides an efficient clean approach broad variety δ‐hydroxy esters also features exceptionally mild conditions, wide compatibility substrate scope functional groups, high atomic economy. Moreover, 1,2‐alkylacylation from same starting materials was achieved one‐pot manner such coupling subsequent two‐electron oxidation process, providing set δ‐keto interest pharmaceutical research.
Language: Английский
Citations
5
Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 3, 2024
Citations
5
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(35), P. 24503 - 24514
Published: Aug. 22, 2024
A facile approach to obtaining densely functionalized cyclopropanes is described. The reaction proceeds under mild conditions via the directed nucleopalladation of nonconjugated alkenes with readily available pronucleophiles and gives excellent yields good anti-selectivity using I2 TBHP as oxidants. Pronucleophiles bearing a diverse collection electron-withdrawing groups, including −CN, −CO2R, −COR, −SO2Ph, −CONHR, −NO2, are well tolerated. Internal alkenes, which generally challenging substrates in other cyclopropanation methods, provide diastereoselectivity this methodology, allowing for controlled access substituted at all three C atoms. DFT calculations mechanistic experiments reveal that major pathway involves initial α-iodination nucleophile, followed by anti-carbopalladation intramolecular C(sp3)–I oxidative addition. Strain-release-promoted C(sp3)–C(sp3) reductive elimination then furnishes cyclopropanated product.
Language: Английский
Citations
4
Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 159, P. 155516 - 155516
Published: Feb. 27, 2025
Language: Английский
Citations
0
Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
Language: Английский
Citations
0
Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101297 - 101297
Published: Feb. 1, 2025
Language: Английский
Citations
0
Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown
Published: April 10, 2025
Herein, we disclose the discovery and development of a site-, regio-, diastereo-, enantioselective aryl C-H bond cyclopropylation using diazomethyl hypervalent iodine reagents, styrenes, paddlewheel dirhodium carboxylate catalysts. A key aspect this work was catalytic generation chiral Rh(II) carbene through an electrophilic aromatic substitution with carbynoids. The strategy allows construction cyclopropane rings bonds from feedstocks drug molecules promises to reach unexplored "cyclopropanated" chemical space highly difficult by current strategies.
Language: Английский
Citations
0