European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Сен. 7, 2024
Abstract Precise deuterium labeling has gained significant attentions owing to the wide applications in organic synthesis, medicinal chemistry, and materials. C−C C‐heteroatom bonds constitute skeleton of molecules. This review summarizes advancements on bond deuterations as well their late‐stage natural products pharmaceutically relevant
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Март 24, 2025
A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective readily available deuterium source is highly desirable. Herein, we report nickel-catalyzed one-pot H/D exchange Michael addition α,β-unsaturated 2-acyl imidazoles with nitromethane in presence D2O. This protocol demonstrates excellent efficiency, high enantioselectivity, broad substrate scope, offering practical versatile approach to accessing deuterium-labeled compounds.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Апрель 3, 2025
Deuterated aryl amines are increasingly sought after in pharmaceuticals, particularly the development of deuterated drugs. Traditional methods for their synthesis often involve harsh conditions or preprepared reagents. This study introduces a mild, metal-free method selective deuteration amines, utilizing deuterium oxide (D2O) and commercially available catalyst, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (NaBArF4). The reaction is performed under moderate compatible with wide range substrates, including sensitive functional groups. Mechanistic studies highlight crucial role noncoordinated Na+ catalysis, underscoring broader potential NaBArF4 weakly coordinating anions (WCAs) synthetic chemistry. offers an efficient sustainable approach to synthesizing amines.
Язык: Английский
Процитировано
0
ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6749 - 6759
Опубликована: Апрель 10, 2025
Язык: Английский
Процитировано
0
Tetrahedron Letters, Год журнала: 2024, Номер 144, С. 155152 - 155152
Опубликована: Июнь 13, 2024
Язык: Английский
Процитировано
3
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Ноя. 24, 2024
Abstract While selective defunctionalizations are valuable in organic synthesis, hydrodeamination of primary amines poses challenges. Deuterodeamination, analogous to hydrodeamination, presents even greater difficulties due its frequently slower deuteration rate, interference by hydrogenation and constraints deuterated sources. This study introduces a reliable, robust, scalable hydro- deuterodeamination method capable handling various amines. Defined mild reaction conditions, rapid completion, simplified purification facilitated water-soluble byproducts, the leverages deuterium oxide as source employs commercialized O-diphenylphosphinylhydroxylamine for deamination. Applied diverse range biologically active molecules, it has consistently achieved high yields efficient incorporation. By synergizing with site-selective C–H functionalization aliphatic amines, our reveals synthetic strategies utilizing nitrogen atom traceless directing group, encompassing deaminative alkylation, 1,1-deuteroalkylation, 1,1-dialkylation, 1,1,1-deuterodialkylation, arylation, 1,3-deuteroarylation. Emphasizing this innovation, processes degree-controlled have been developed.
Язык: Английский
Процитировано
3
Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(16), С. 4479 - 4486
Опубликована: Янв. 1, 2024
A highly selective photocatalytic deuterodefluorination of α, α -difluoroarylacetic esters and amides with D 2 O is presented. The use a catalytic amount disulfide crucial for both the C–F bond activation C–D formation.
Язык: Английский
Процитировано
2
Green Chemistry, Год журнала: 2024, Номер 26(7), С. 3767 - 3775
Опубликована: Янв. 1, 2024
The combination of three types catalysts in one pot, including borate, palladium, and lipase, enabled a one-pot β-specific methylene C(sp 3 )–H deuteration reaction aliphatic acids using D 2 O.
Язык: Английский
Процитировано
1
Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown
Опубликована: Июнь 1, 2024
Hydrogen-deuterium exchange (HIE) reaction is the most direct way to achieve deuterium labeling as there no need for extra pre-functionalization. Herein, we report an electrochemical selective labelling of N-heteroarenes using D2O. The formation aromatic radicals has been directly identified by time-resolved electron paramagnetic resonance (EPR) technique under conditions. Mechanistic studies revealed that hydrogen/deuterium (H/D) involved continuous redox paired electrolysis and selectivity deuteration was established DFT calculations. This synthesis method offers a promising avenue incorporation at specific sites compounds.
Язык: Английский
Процитировано
1
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(37), С. 7596 - 7600
Опубликована: Янв. 1, 2024
A straightforward copper-catalyzed deborodeuteration of arylboronic acids and borates was achieved, employing the cost-effective deuterium source D
Язык: Английский
Процитировано
1
Angewandte Chemie, Год журнала: 2024, Номер unknown
Опубликована: Сен. 30, 2024
Abstract Es wird ein hochgradig regioselektiver, von sichtbarem Licht photoredox‐katalysierter Wasserstoff‐isotopenaustausch (WIA) an benzylischen Positionen einfachen und komplexen Molekülen beschrieben. Der Prozess folgt einem dual katalytischen Ansatz, basierend auf der Kombination eines Acridinium‐Photokatalysators mit Thiol basierten Wasserstoffatomtransfer Katalysator (HAT). Die Verwendung D 2 O als Isotopenquelle gewährleistet hierbei eine einfache Handhabung Kosteneffizienz. konnte hohe Reaktivität für elektronenreiche benzylische erreicht werden. gezielte Bildung Radikalen ermöglicht einen selektiven WIA intramolekular konkurrierenden Benzyl‐ alpha zu Heteroatom‐positionen moderatem bis ausgezeichnetem Deuteriumeinbau. Nutzen dieser Reaktion wurde durch verschiedenen Naturstoff‐ Arzneimittelderivaten demonstriert. Experimentelle Studien Dichtefunktionaltheorieberechnungen (DFT) legen Ein‐Elektronen‐Übertragungsmechanismus (SET) nahe, gefolgt einer Deprotonierung zur des Radikals. Hierbei die Bedeutung halogenierten Lösungsmitteln oder Additiven demonstriert schwache Interaktion Halogenspezies dem Substrat führt Komplexes. Dies resultiert in Senkung Oxidationspotenzials Stabilisierung Radikal‐Kation‐Spezies Spin‐Delokalisierung.
Процитировано
1