Synthesis of Lactams via a Chiral Phosphoric Acid-Catalyzed Aniline Cyclization DOI Creative Commons

Abigail H. Horchar,

Jonathan E. Dean,

Alexander R. Lake

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12725 - 12738

Опубликована: Авг. 9, 2024

The enantioenriched lactams disclosed in this work are synthesized concisely four steps. In the penultimate reaction, a benzylamine species complexes with chiral phosphoric acid to produce benzo-fused δ-lactams equipped an all-carbon quaternary stereocenter. Partial and full reductions were carried out on ester amide moieties, Suzuki–Miyaura cross-coupling expanded molecule from aromatic ring. Finally, our method was successful at >1 g scale, indicating that has important practical use.

Язык: Английский

A ratiometric turn-on fluorescent probe for the detection of BF3 based on imidazole-quinoline DOI
Shasha Wu, Lei Sun,

Yeping Bian

и другие.

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, Год журнала: 2025, Номер 332, С. 125748 - 125748

Опубликована: Янв. 13, 2025

Язык: Английский

Процитировано

0

BF3·Et2O-promoted unconventional reactions of 2-oxoaldehyde: access to 4-amidooxazoles and β-keto amides/sulphonamides DOI

Ashiq Hussain Padder,

Bhawna Ghora,

Feroze Hussain

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This study investigates the potential of boron trifluoride etherate (BF3·OEt2) to trigger unprecedented reactions 2-oxoaldehydes with nitriles and amides/sulphonamides. In contrast mechanism in conventional reactions, α-carbonyl group induces a cyclization pathway be followed when reacting nitriles, yielding 4-amidooxazoles. Additionally, weak nucleophiles produce β-keto BF3·OEt2 catalysis offers novel, efficient, operationally simple synthetic route these valuable compounds, showcasing versatility Lewis acids organic transformations.

Язык: Английский

Процитировано

0

Intramolecular Fluoroacylation Enabled by TrBF4-Catalyzed Fluoride Recycling DOI

Alice A. Mcknight,

Yuriko H. Fujisato,

Namrata Khanal

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 27, 2025

Alkyne- and alkene-tethered acyl fluorides undergo intramolecular carbofluorination via fluoride recycling using catalytic TrBF4. Excellent stereoselectivity is observed for the alkyne addition, enabling access to novel fluorinated indan-2-ones (all ≥95:5 E/Z) cyclopentan-2-ones (85:15 E/Z). Fluorinated chroman-2-ones tertiary alkyl can also be synthesized this method, comparing favorably previously reported protocols that employ expensive metal catalysts under harsher conditions.

Язык: Английский

Процитировано

0

Guanidium Unmasked: Repurposing Common Amide Coupling Reagents for the Synthesis of Pentasubstituted Guanidine Bases DOI Creative Commons

Juhana A. S. Aho,

Jere K. Mannisto, S Mattila

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 11, 2025

Guanidines make up a class of compounds with important applications in catalysis and medicinal chemistry. In this systematic study, we report on the guanylation aliphatic amines, anilines, (sulfon)amides, ureas, carbamates by repurposing HATU, common amide coupling reagent. The products are 2-substituted 1,1,3,3-tetramethylguanidines (TMGs), group sterically hindered superbases. reaction guanidinium salt amines has been regarded as an unwanted side-reaction coupling, yet exact mechanistic details have unclear. Our investigation shows that is highly dependent nature nitrogen nucleophile. findings were applied two fronts: minimizing competing reactions well maximizing simple one-step synthesis broad variety TMGs, including late-stage functionalization pharmaceuticals.

Язык: Английский

Процитировано

0

Oxidation of Difluorocarbene by Pyridine N‐Oxide and Ensuing Access to Carbamoyl Fluorides DOI

Haijun Tang,

Xue‐Min Shi,

Xiaoyu Zhu

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(22), С. 2981 - 2987

Опубликована: Июнь 30, 2023

Comprehensive Summary A practical one‐pot preparation of carbamoyl fluorides from easily obtained pyridine N ‐oxide, commercially available secondary amines and synthetically versatile difluorocarbene precursors (Ruppert‐Prakash reagent or Chen's reagent) was developed herein, which dexterously resorted to the oxidation by external ‐oxide produce toxic gaseous fluorophosgene in situ . Notable features this method include nice functionality tolerance, late‐stage modification drug molecules recovery recycle quinoline.

Язык: Английский

Процитировано

7

Non-Classical Molecular Activation by Phosphines and N-Heterocyclic Carbenes and Its Application to Catalytic Reactions DOI
Hayato Fujimoto, Kosuke Yasui, Mamoru Tobisu

и другие.

Bulletin of the Chemical Society of Japan, Год журнала: 2023, Номер 96(9), С. 872 - 886

Опубликована: Июль 27, 2023

Abstract This Award Account reports our recent studies concerning the catalytic transformations that involve a non-classical mode of molecular activation by tertiary phosphines and N-heterocyclic carbenes (NHCs). Regarding organophosphine catalysis, we successfully designed reactions based on P(III)/P(V) redox couple. A protocol for generating pentacoordinate P(V) species was devised reaction phosphines, acyl fluorides alkynoates. The ability thus generated fluorophosphoranes to participate in ligand coupling metathesis with organosilicon nucleophiles enables synthetic are otherwise unattainable, including intermolecular carbofluorination alkynes hydroalkenylation enol ethers. nucleophilic NHC use imidazolium-based NHCs can generate deoxy-Breslow intermediates sufficiently promote aromatic substitution aryl halides, ethers anilides. also be used styrene derivatives, allowing generation series ylide serve as non-stabilized vinyl anion equivalents. These results demonstrate involving carbanions conducted under conditions without strong organometallic nucleophiles.

Язык: Английский

Процитировано

6

Visible-Light-Induced DDQ-Catalyzed Fluorocarbamoylation Using CF3SO2Na and Oxygen DOI

H. E. Cho,

Seonga Jang,

Kangjoo Lee

и другие.

Organic Letters, Год журнала: 2023, Номер 25(48), С. 8558 - 8563

Опубликована: Ноя. 21, 2023

The synthesis of carbamoyl fluorides via visible-light induced DDQ catalysis secondary amines is described. This protocol employs sodium trifluorosulfinate and molecular oxygen for the in situ generation carbonyl difluoride, which reacted with to afford corresponding efficiently. Moreover, are easily transformed synthetically useful compounds under mild reaction conditions.

Язык: Английский

Процитировано

6

C-F insertion reaction sheds new light on the construction of fluorinated compounds DOI
Dongsheng Deng,

Su-Qin Tang,

Yong-Tu Yuan

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 35(8), С. 109417 - 109417

Опубликована: Дек. 21, 2023

Язык: Английский

Процитировано

4

Pd-Catalyzed Suzuki-Type Cross-Coupling of 2-Pyridyl Carbamoyl Fluorides DOI

Maryam Jabbarpoor,

Jesse LeBlanc,

Zichuan Chen

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(66), С. 8700 - 8703

Опубликована: Янв. 1, 2024

We describe a palladium-catalyzed Suzuki-type cross-coupling reaction of 2-pyridyl carbamoyl fluorides with boronic acids, which provides entry to medicinally relevant pyridyl amides. Mechanistic studies, including the synthesis and reactivity Pd-F complexes, reveal importance both fluoride electrophile nitrogen directing group for aiding reactivity.

Язык: Английский

Процитировано

1

Catalytic HF Shuttling between Fluoroalkanes and Alkynes** DOI Creative Commons

Shannon E. S. Farley,

Daniel Mulryan,

Feriel Rekhroukh

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(5)

Опубликована: Дек. 9, 2023

Abstract In this paper, we report BF 3 ⋅ OEt 2 as a catalyst to shuttle equivalents of HF from fluoroalkane an alkyne. Reactions terminal and internal aliphatic alkynes led formation difluoroalkane products, while diarylalkynes can be selectively converted into fluoroalkenes. The method tolerates numerous sensitive functional groups including halogen, protected amine, ester thiophene substituents. Mechanistic studies (DFT, probe experiments) suggest the is involved in both defluorination fluorination steps, with acting Lewis acid weak base that mediates proton transfer. certain cases, interconversion fluoroalkene products was found reversible. new catalytic system applied demonstrate proof‐of‐concept recycling poly(vinylidene difluoride).

Язык: Английский

Процитировано

3