Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519
Published: Jan. 1, 2024
Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile
Language: Английский
Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1483 - 1488
Published: Feb. 12, 2024
Presented herein is a palladium-catalyzed asymmetric (3 + 2) annulation reaction between 1,3-dienes and 2-formylarylboronic acids, proceeding in cascade vinylogous addition Suzuki coupling process. Both electron-neutral electron-deficient are compatible under similar catalytic conditions, distinct regioselectivity observed via functional-group control of 1,3-diene substrates. A collection 1-indanols with dense functionalities constructed stereoselectively.
Language: Английский
Citations
3
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(24)
Published: Feb. 21, 2024
In this paper, Pd-catalyzed [4+2] decarboxylative cycloaddition of 4-vinylbenzodioxinones with barbiturate-derived alkenes has been developed, leading to various spirobarbiturate-chromane derivatives in high yields excellent diastereo- and enantioselectivities. The scale-up reaction further derivation the product were demonstrated. A plausible mechanism was also proposed.
Language: Английский
Citations
3
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(17), P. 12824 - 12832
Published: Aug. 10, 2024
Here, we demonstrate that Pd(0) can undergo direct oxidative addition to electron-deficient 1-azadienes without the additional assistance of Lewis or Bro̷nsted acids, and resultant azapalladacycle species undertake migratory insertion into allenes with exclusive C2-regioselectivity. Fine dynamic kinetic transformation is achieved in subsequent N-allylic alkylation situ formed π-allylpalladium intermediates from racemic allenes, high levels enantioselectivity are generally obtained for tetrahydropyridine products an E-exo-double bond a (4 + 2) annulation pattern. Moreover, switchable regiodivergent 1) annulations different types be accomplished via ligand control. In addition, similar oxapalladacycles activated enones generated assembled access dihydropyran derivatives enantioselectively, further enriching diversity-oriented synthesis. An array control experiments spectroscopic analyses conducted confirm formation these unusual heteropalladacycle intermediates, density functional theory (DFT) calculations carried out illuminate catalytic pathways.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8951 - 8959
Published: May 30, 2024
Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.
Language: Английский
Citations
1
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5495 - 5501
Published: Jan. 1, 2024
Rhodium( i )-catalyzed sequential decarboxylation and hydroacylation of vinyl benzoxazinanones with chelating aldehydes for the highly regioselective synthesis 2-substituted indolines via a new η 2 -Rh complex has been developed.
Language: Английский
Citations
1
Nature Synthesis, Journal Year: 2023, Volume and Issue: 3(3), P. 329 - 336
Published: Nov. 9, 2023
Language: Английский
Citations
3
Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)
Published: Nov. 28, 2023
Abstract A regioselective annulation protocol of N ‐chlorobenzamide with allenes and vinyl acetate is reported using a less expensive catalytic system, i. e . Co(III) catalysis Na 2 CO 3 as base. (CO) NH−Cl acts both, an internal oxidant directing group. Allenes are successfully annulated ‐chlorobenzamide, providing different exocyclic isoquinolone derivatives in good to moderate yield. Notably, acetylene surrogate undergoes the developed provide excellent Interestingly, situ deprotection acetyl group allowed quantitative synthesis hydroxyisoquinolone.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375
Published: June 7, 2024
Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.
Language: Английский
Citations
0
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519
Published: Jan. 1, 2024
Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile
Language: Английский
Citations
0