Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
This review gives an overview of the C–H functionalisation azoles via Minisci-type reactions, highlighting recent progress, existing limitations and potential areas for growth.
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(35), С. 7447 - 7451
Опубликована: Авг. 24, 2024
The merging of electrochemistry and photocatalysis allowed the required selectivity for hydroxymethylation functionalized azaarenes with methanol, including bioactive substrates. two electrophotocatalytic protocols developed in this work address transformation, using nontoxic readily available reagents under mild reaction conditions electricity as only "sacrificial oxidant".
Язык: Английский
Процитировано
3
ACS Catalysis, Год журнала: 2025, Номер unknown, С. 3499 - 3504
Опубликована: Фев. 12, 2025
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Фев. 27, 2025
In this work, we developed a general catalytic strategy that allows Minisci C-H alkylation of variety heterocycles using unactivated alkyl halide as an radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN organophotocatalyst and aerial oxygen green terminal oxidant, broad scope, good functional group tolerance, late-stage bioactive pharmaceutically relevant molecules are advantages the protocol. Preliminary mechanistic studies indicate involvement α-amino further our conditions.
Язык: Английский
Процитировано
0
Communications Chemistry, Год журнала: 2025, Номер 8(1)
Опубликована: Март 29, 2025
The functionalization of challenging unactivated C(sp3)–H bonds was achieved electrocatalytically via hydrogen atom transfer and without mediators. This possible through the sole activation surface Glassy Carbon Electrode (GCE) in an electrochemical fashion using a phosphate buffer. produced oxygenated functional groups on surface, capable abstracting these atoms from alkanes. Minisci Ritter-type reactions were this procedure. Extensive characterization activated GCE (AGCE) preliminary mechanistic studies allow us to propose plausible reaction mechanisms. Furthermore, regular battery can be used within protocol achieve desired substituted alkanes under inexpensive user-friendly conditions. Aliphatic compounds play crucial role pharmaceutical agrochemical industries, however, selective modification structures remains due high strength bonds. Here, authors report Minisci-type alkylation azaarenes with Ritter between nitriles glassy carbon electrode, achieving electrocatalytic inert that eliminates need for traditional mediators or metals.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Апрель 7, 2025
A highly efficient 6-endo-trig radical cyclization reaction between cyclobutanone oximes and 1-isocyano-2-vinylbenzenes via visible light-induced photoredox catalysis has been realized in the presence of 2 mol % fac-Ir(ppy)3 as photocatalyst, which gave rise to a variety 2-(3-cyanoalkyl)substituted quinoline derivatives with moderate excellent yields under mild conditions.
Язык: Английский
Процитировано
0
Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 13(4)
Опубликована: Дек. 23, 2023
Abstract Hydrogen‐atom transfer (HAT) catalysis offers an atom‐ and step‐economical approach to the direct functionalization of aliphatic C−H bonds. While structure HAT catalysts largely affects reactivity selectivity in step where bond is cleaved, choice viable for from strong bonds limited. The recent development organic based on flexibly modifiable molecular platform has enabled fine‐tuning steric electronic properties these catalysts, thus greatly expanding their structural diversity. This review focuses design with cationic moieties as common motifs application selective manipulation challenging substrates, including unactivated hydrocarbons.
Язык: Английский
Процитировано
8
Опубликована: Май 31, 2024
The merge of electrochemistry and photocatalysis allowed the required selectivity for hydroxymethylation functionalized azaarenes with methanol, including bioactive substrates. two electrophotocatalytic protocols developed in this work address transformation, using non-toxic readily available reagents under mild reaction conditions electricity as only “sacrificial oxidant.”
Язык: Английский
Процитировано
2
Organic Letters, Год журнала: 2023, Номер 25(51), С. 9219 - 9224
Опубликована: Дек. 19, 2023
The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1,6-enynes were developed. A series cyclopropane-fused hetero- and carbo-bicyclic, tricyclic, spiro-tetracyclic compounds facilely synthesized from a broad scope 2,6-lutidine N-oxide under mild metal-free conditions with blue light-emitting diode light irradiation. reaction occurs the intermediacy β-oxyvinyl radical, which is produced photocatalytically generated pyridine N-oxy addition to carbon–carbon triple bond.
Язык: Английский
Процитировано
4
ACS Catalysis, Год журнала: 2024, Номер 14(19), С. 14574 - 14585
Опубликована: Сен. 16, 2024
A class of in-situ generated Lewis acid (LA) activated acridine complexes is reported, which act as potent photochemical catalysts for the oxidation a variety protected secondary amines. Acridine/LA exhibit tunable excited state reduction potentials ranging from +2.07 to 2.38 V vs. SCE. The ytterbium triflate complex 3,6-di-t-butyl-9-mesitylacridine catalyzes Giese-type reaction Boc-protected amines with challenging conjugate acceptors such acrylates, that are inaccessible analogous acridinium (t-Bu-Mes-Acr⊕) catalyzed reaction. mechanism this was investigated using suite physical organic probes including intramolecular 13C kinetic isotope effects (KIEs), variable time normalization analysis (VTNA) kinetics, determination redox potentials, and computational studies. In by t-Bu-Mes-Acr⊕, mechanistic studies consistent single-electron transfer (SET) ground-state reduced t-Bu-Mes-Acr• α-keto radical intermediate first irreversible step in catalytic cycle. Intriguingly, we find acridine/LA better ground reductants (-0.72 -0.74 vs SCE) relative (-0.59 predict increased substrate reactivity stems lower energy barrier key SET event.
Язык: Английский
Процитировано
1
ACS electrochemistry., Год журнала: 2024, Номер unknown
Опубликована: Ноя. 27, 2024
Язык: Английский
Процитировано
1