Carbohydrate Research, Journal Year: 2023, Volume and Issue: 536, P. 109018 - 109018
Published: Dec. 23, 2023
Language: Английский
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(10), P. 6422 - 6437
Published: March 1, 2024
The development of a new catalytic strategy plays vital role in modern organic chemistry since it permits bond formation an unprecedented and more efficient manner. Although the application preformed metal complexes as π-base-activated reagents have enabled diverse transformations elegantly, concept by directly utilizing transition metals π-Lewis base catalysts remain underdeveloped, especially field asymmetric catalysis. Here, we outline our perspective on discovery palladium(0) catalyst, which is capable increasing highest occupied molecular orbital (HOMO) energy both electron-neutral electron-deficient 1,3-dienes 1,3-enynes upon flexible η2-complexes formed situ resultant π-backdonation. Thus, fruitful carbon–carbon-forming reactions with electrophiles can be achieved enantioselectively vinylogous addition pattern, conceptually different from classical oxidative cyclization mechanism. Emphasis will given to mechanism elucidation, features, reaction design together further this emerging field.
Language: Английский
Citations
14
Chemical Science, Journal Year: 2023, Volume and Issue: 14(8), P. 2082 - 2090
Published: Jan. 1, 2023
We report a combined experimental and computational study of Pd/Senphos-catalyzed carboboration 1,3-enynes utilizing DFT calculations, 31P NMR study, kinetic Hammett analysis Arrhenius/Eyring analysis. Our mechanistic provides evidence against the conventional inner-sphere β-migratory insertion mechanism. Instead, syn outer-sphere oxidative addition mechanism featuring Pd-π-allyl intermediate followed by coordination-assisted rearrangements is consistent with all observations.
Language: Английский
Citations
12
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11778 - 11792
Published: Aug. 9, 2023
An efficient, secondary amine-catalyzed cascade annulation of 2-O/N-propargylarylaldehydes with 2,6-dialkylphenols was established to access biologically relevant functionalized 2H-chromenes and 1,2-dihydroquinolines tethered a synthetically useful p-quinone methide scaffold in high yields under microwave irradiation conventional heating conditions. The microwave-assisted strategy convenient, clean, rapid, yielding which the reactions were completed just 15 min, obtained up 95%. This highly atom-economical domino process constructed two new C-C double bonds six-membered O/N-heterocyclic ring single synthetic operation. Its mechanism rationalized as involving sequential iminium ion formation, nucleophilic addition, intramolecular steps. Furthermore, synthesized 2H-chromene derivatives transformed into valuable indeno[2,1-c]chromenes, 5H-indeno[2,1-c]quinolines, oxireno[2,3-c]chromene via palladium-catalyzed C-H bond activation epoxidation, respectively.
Language: Английский
Citations
6
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(69), P. 9278 - 9281
Published: Jan. 1, 2024
The synthesis of bis-lactone and butenolide derivatives was described using alkylidene Meldrum's acid as nucleophiles. process operates in a triple cascade through an auto tandem catalysis promoted by DBU.
Language: Английский
Citations
1
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
A palladium-catalysed three-component reaction between 1,3-enynes, 2-formylphenylboronic acids and N -sulfonyl amines has been developed, furnishing a variety of multifunctional benzofulvenes in moderate to good yields E / Z -selectivity.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6523 - 6528
Published: July 19, 2024
An enantioselective addition reaction of alkynyl esters with imines was developed under asymmetric autotandem catalysis a chiral Brønsted base. A bis(guanidino)iminophosphorane organosuperbase, which has much higher basicity than that conventional organic bases, efficiently promoted both the intramolecular cyclization for construction benzofuran ring or benzothiophene and sequential direct Mannich-type diarylmethane derivatives, affording enantio-enriched diarylalkane derivatives are otherwise difficult to access.
Language: Английский
Citations
1
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3300 - 3306
Published: Jan. 1, 2023
Substrate-controlled divergent cascade reactions between ortho -vinyl-functionalised 1,3-enynes and imines have been realised via palladium catalysis, furnishing collections of skeletally distinct architectures in good yields stereoselectivity.
Language: Английский
Citations
3
Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(6)
Published: May 18, 2023
Abstract Presented herein is a palladium catalyzed tandem reaction between 3‐aminoethyl group tethered 1,3‐enynes and imines, proceeding through cascade vinylogous addition/reductive elimination/protonation/allylic amination 1,3‐hydrogen transfer sequence. A collection of complex hexahydro‐1 H ‐pyrrolo[3,2‐ c ]pyridine architectures were straightforwardly constructed in moderate yields diastereoselectivity.
Language: Английский
Citations
2
Journal of Heterocyclic Chemistry, Journal Year: 2023, Volume and Issue: 60(11), P. 1872 - 1882
Published: Aug. 23, 2023
Abstract A mild and effective method for the synthesis of 3‐sulfonyl‐1,2‐dihydroquinolines from N ‐acyl‐protected 2‐aminobenzaldehyde with vinyl sulfones has been established. This reaction could rapidly proceed exhibit different reactivity when employed as nucleophile on aza‐Michael addition/cyclization reaction, allow production 1,2‐DHQs in high yields up to 95%. In addition, chemical structure product was confirmed by x‐ray single‐crystal analysis.
Language: Английский
Citations
1
Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 493 - 568
Published: Jan. 1, 2023
Language: Английский
Citations
0