Synfacts, Journal Year: 2022, Volume and Issue: 19(01), P. 0060 - 0060
Published: Dec. 16, 2022
Key words palladium - organoboron catalysis dual azoles allylation
Language: Английский
Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1722 - 1726
Published: March 4, 2023
Direct N-allylation of azoles with hydrogen evolution has been achieved through the synergistic combination organic photocatalysis and cobalt catalysis. The protocol bypasses stoichiometric oxidants prefunctionalization alkenes produces (H2) as byproduct. This transformation highlights high step- atom-economy, efficiency, broad functional group tolerance for further derivatization, which opens a door C-N bond formation that is valuable in heterocyclic chemistry.
Language: Английский
Citations
19
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(7), P. 4973 - 4984
Published: Feb. 8, 2024
In the presence of an arylboronic acid catalyst, azole-type heterocycles, including purines, tetrazoles, triazoles, indazoles, and benzo-fused congeners, undergo regio- stereoselective N-glycosylations with furanosyl pyranosyl trichloroacetimidate donors. The protocol, which does not require stoichiometric activators, specialized leaving groups, or drying agents, provides access to nucleoside analogues enables late-stage N-glycosylation azole-containing pharmaceutical agents. A mechanism involving simultaneous activation glycosyl donor acceptor by organoboron catalyst has been proposed, supported kinetic analysis computational modeling.
Language: Английский
Citations
8
Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3966 - 3971
Published: April 26, 2024
Here we report the first example of iridium-catalyzed asymmetric
Language: Английский
Citations
4
Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1638 - 1641
Published: Jan. 1, 2024
A practical one-pot catalytic tandem multicomponent allylation condensation carbonylation to construct allylhydrazones and allyl acylhydrazones with high atom economy, water as a coproduct excellent regioselectivity in reactions.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1320 - 1330
Published: Jan. 9, 2024
Novel imidazole-containing boronic acid and palladium hybrid catalysis for regioselective O-allylation of carbohydrates has been developed. This catalytic process enables the introduction a useful allyl functional group into equatorial hydroxy cis-1,2-diols various with low catalyst loading excellent regioselectivities. is first report on in combination Lewis base-containing transition metal complex.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: April 25, 2025
Methods for regioselective ring-opening reactions of N-sulfonyl-protected aziridyl alcohols with azole nucleophiles have been developed. Several classes azoles, including indazole, substituted pyrazole, benzotriazole, and tetrazole, employed as reaction partners, giving rise to C3-selective opening >3:1 N-selectivity. BF3•OEt2 is the optimal catalyst most substrate combinations, although examples where diphenylborinic acid (Ph2BOH) provides higher yields, or proceed efficiently without a catalyst, are also described. Computational modeling BF3•OEt2-catalyzed consistent observed regiochemical outcome. The calculated transition state appears be stabilized by an unconventional OH···FB hydrogen-bonding interaction.
Language: Английский
Citations
0
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 6728 - 6739
Published: April 16, 2024
In the presence of Pd(Xantphos) and an electron-deficient arylboronic acid cocatalyst, azoles such as pyrazoles, triazoles, tetrazoles, purines undergo regioselective, dehydrative allylations with allylic alcohols. The boronic has a significant effect on both rate regioselectivity these reactions. Herein, combined experimental computational mechanistic study synergistic organoboron- palladium-catalyzed allylation is described. Kinetic analysis evaluation effects substitution reaction point toward turnover-limiting ionization alcohol, Lewis activation by acid. Computational modeling pathway density functional theory indicates that alcohol also regioselectivity-determining step resulting ion pair undergoes C–N bond formation through outer-sphere mechanism. An unexpected observation autocatalysis emerged from kinetic motivated additives, leading to development improved protocol.
Language: Английский
Citations
2
Organic Letters, Journal Year: 2023, Volume and Issue: 25(46), P. 8274 - 8278
Published: Nov. 14, 2023
Synergistic organoboron/palladium cocatalysis enables dehydrative couplings of NH-sulfoximines with allylic alcohols, furnishing the corresponding N-allylated products. The reactions proceed in absence a Brønsted base and are tolerant diverse sulfoximine partners, including functionalized variants. Experimental computational studies suggest that reagent is activated by complexation to boronic acid cocatalyst.
Language: Английский
Citations
5
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(18)
Published: Feb. 15, 2024
Abstract This report describes the one‐pot direct N ‐acylation of indazole with carboxylic acids using our previously developed 4‐( , ‐dimethylamino)pyridine ‐oxide (DMAPO)/di‐ tert ‐butyl dicarbonate (Boc 2 O) system. simple system provides 1‐acyl indazoles in high yield 1 selectivities and does not require use activated derivatives or temperatures. new method exhibits a wide substrate scope (>40 examples). In addition, synthesis 1‐functionalized alkyl utilizing as starting materials was achieved. stepwise protocol is useful for selective structurally diverse indazoles, which are difficult to synthesize by other methods such Mitsunobu reaction classical S alkylation indazole.
Language: Английский
Citations
1
Tetrahedron, Journal Year: 2024, Volume and Issue: 158, P. 133991 - 133991
Published: April 15, 2024
Language: Английский
Citations
1