Molecules, Journal Year: 2023, Volume and Issue: 28(16), P. 5975 - 5975
Published: Aug. 9, 2023
The field of Organic Chemistry represents one the most traditional areas chemistry that has delivered many benefits to community chemists [...]
Language: Английский
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 10, 2025
Diastereoselective synthesis of trans-3,4-difunctionalized tetrahydroquinoline and chromane derivatives via the oxo-sulfonylation 1,7-enynes is demonstrated. The reaction involves a three-component oxidative radical polar crossover (ORPC) approach wherein vinyl carbocation intermediate undergoes nucleophilic substitution to afford corresponding keto functional group. Deprotection N-Ts group, gram-scale synthesis, other synthetic applications were illustrated. Control experiments mechanistic studies show that water acts as nucleophile in this reaction.
Language: Английский
Citations
1
Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)
Published: April 8, 2023
Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.
Language: Английский
Citations
23
Molecules, Journal Year: 2023, Volume and Issue: 28(7), P. 3027 - 3027
Published: March 28, 2023
Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction functional groups. In radical difunctionalization reactions, radicals first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, ring opening. The resulting undertake following paths second functionalization: (1) couple with other groups, (2) oxidize to cations then react nucleophiles, (3) reduce anions electrophiles, (4) metal-complexes. rearrangements provide opportunity 1,3-, 1,4-, 1,5-, 1,6-, 1,7-difunctionalization products. Multiple ways initiate reaction coupling intermediate make reactions good at remote positions. These offer advantages synthetic efficiency, operation simplicity, product diversity.
Language: Английский
Citations
21
Organic Letters, Journal Year: 2023, Volume and Issue: 25(21), P. 3910 - 3915
Published: May 24, 2023
An efficient aminofluorosulfonylation strategy was developed for the synthesis of various pyrazoline-functionalized aliphatic sulfonyl fluorides using β,γ-unsaturated hydrazones with sulfur dioxide and NFSI as starting materials under mild conditions. The fluoride products could be successfully transformed into corresponding sulfonate esters amides via sulfur(VI) exchange (SuFEx) click reactions. Preliminary mechanistic investigations demonstrate that reaction operates through a radical cyclization/SO2 insertion/fluorination cascade process.
Language: Английский
Citations
14
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(35), P. 7079 - 7084
Published: Jan. 1, 2023
Polychloromethylative cyclization of N-alkenyl indoles was developed under metal-free conditions to afford tricyclic pyridoindolones and pyrroloindolones in moderate good yields. In the reaction, commercially available CHCl3 CH2Cl2 were employed as tri- dichloromethyl radical sources. Moreover, dichloromethylated polycyclic benzoimidazoles can also be obtained standard conditions.
Language: Английский
Citations
9
European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(46)
Published: Oct. 30, 2023
Abstract Photo‐induced sulfonylamidation/lactonization of alkenyl acids with N ‐sulfonylaminopyridinium salts is demonstrated to access sulfonamidylated lactones under mild and metal‐free conditions. This reaction features a broad substrate scope, good functional group tolerance easy operation, providing simple efficient protocol for the synthesis lactones.
Language: Английский
Citations
4
Molecules, Journal Year: 2024, Volume and Issue: 29(11), P. 2559 - 2559
Published: May 29, 2024
Radical reactions are powerful in the synthesis of diverse molecular scaffolds bearing functional groups. In previous review articles, we have presented 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6- and 1,7-difunctionalizations, addition followed by cyclization reactions. Presented this paper is radical second functionalization reaction. The could be realized atom transfer reactions, or transition metal-assisted coupling with neutral molecules, cationic anionic species.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: unknown
Published: Dec. 9, 2024
We report a radical cyano-cyclization of 1,6-enynes with isonitriles via photochemically driven nickel catalysis, forging alkenyl nitrile-tethered γ-lactams under mild conditions. This reaction leverages the photoexcitation
Language: Английский
Citations
1
ChemCatChem, Journal Year: 2024, Volume and Issue: unknown
Published: May 16, 2024
Abstract The synthesis of acylmethylatated pyrrolo‐quinazolinones was developed via photo‐induced cascade radical addition/cyclization N ‐(but‐3‐enyl)quinazolin‐4(3 H )‐ones with sulfoxonium ylides using 4CzIPN as the photocatalyst. This approach also suitable for construction piperidino‐quinazolinones. protocol features mild conditions, convenient operation, broad substrate scope and good functional group compatibility.
Language: Английский
Citations
0
Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3620 - 3620
Published: July 31, 2024
Synthetic radicals have intrinsic power for cascading and multifunctional reactions to construct diverse molecular scaffolds. In the previous review series, we covered 1,2-difunctionalizations, remote 1,3-, 1,4-, 1,5-, 1,6-, 1,7-difunctionalizations, addition followed by cyclization reactions, cycloaddition-initiated difunctionalizations. Presented in this paper are radical addition-initiated trifunctionalization of alkenes, alkynes, their derivatives. After initial addition, there different pathways, such as group or hydrogen atom transfer, cyclization, coupling, complete second third functionalizations.
Language: Английский
Citations
0