Chemistry - An Asian Journal, Год журнала: 2025, Номер unknown
Опубликована: Март 12, 2025
Abstract A copper‐catalyzed remote 1,5‐trifluoromethyl thio(seleno)cyanation of 5‐hexenenitriles with an intramolecular cyano migration has been established, affording a variety CF 3 /CN‐containing thiocyanates and selenocyanates under mild conditions. The reaction features high chemo‐ regioselectivities illustrates potential value in synthetic chemistry.
Язык: Английский
Chemistry - A European Journal, Год журнала: 2023, Номер 29(52)
Опубликована: Июнь 28, 2023
Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.
Язык: Английский
Процитировано
54
Green Chemistry, Год журнала: 2021, Номер 23(2), С. 1041 - 1049
Опубликована: Янв. 1, 2021
A
copper
modified
phosphorus
doped
g-C3N4
(Cu/P-CN)
has
been
prepared
and
identified
as
an
efficient
catalyst
for
the
synthesis
of
Язык: Английский
Процитировано
73
Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(4), С. 398 - 462
Опубликована: Янв. 18, 2023
Abstract The difunctionalizative trifluoromethylation of unsaturated C−C bonds is a highly useful and efficient method for the synthesis trifluoromethyl compounds with attractive architectures from simple feedstocks, allowing introduction CF 3 group along wide variety substituents either inter‐ or intramolecularly. Given that molecules are increasingly used as promising bioactive species in design new drugs agrochemicals, has been extensively studied during last decade. This review focuses on reactions proceeding via simultaneous formation C−heteroatom (O, N, S, Se, B) C−H bonds, these provide group‐containing building blocks. To identify trends prospects evolution this methodology, we systematically describe variants types more general view reaction conditions, modes, mechanisms. presented comprehensive survey enables categorization into those synthetically mature room further development. magnified image
Язык: Английский
Процитировано
39
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5783 - 5796
Опубликована: Апрель 9, 2024
A visible-light-induced radical-cascade selenocyanation/cyclization of N-alkyl-N-methacryloyl benzamides, 2-aryl-N-acryloyl indoles, and N-methacryloyl-2-phenylbenzimidazoles with potassium isoselenocyanate (KSeCN) was developed. The reactions were carried out inexpensive KSeCN as a selenocyanation reagent, persulfate an oxidant, 2,4,6-triphenylpyrylium tetrafluoroborate bifunctional catalyst for phase-transfer catalysis, photocatalysis. library selenocyanate-containing isoquinoline-1,3(2H,4H)-diones, indolo[2,1-a]isoquinoline-6(5H)-ones, benzimidazo[2,1-a]isoquinolin-6(5H)-ones achieved in moderate to excellent yields at room temperature under visible-light ambient conditions. Importantly, the present protocol features mild reaction conditions, large-scale synthesis, simple manipulation, product derivatization, good functional group, heterocycle tolerance.
Язык: Английский
Процитировано
11
Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(12), С. 3201 - 3232
Опубликована: Ноя. 5, 2021
Abstract Olefins are synthetically useful building blocks in modern organic synthesis. Direct functionalization of olefins; represent one the most explored transformations synthetic chemistry due to their easy availability and reactivity towards large number reactants affording diverse range compounds. In recent times, development new protocols for olefins is a growing realm. A plethora olefin methodologies have been reported literature through ionic free radical mechanisms including single electron transfer (SET) last two decades. This review gives an overview mono‐ difunctionalization unactivated olefins, with emphasis on mechanistic details.
Язык: Английский
Процитировано
52
Journal of the Energy Institute, Год журнала: 2021, Номер 99, С. 229 - 239
Опубликована: Сен. 30, 2021
Язык: Английский
Процитировано
48
The Chemical Record, Год журнала: 2021, Номер 21(10), С. 2739 - 2761
Опубликована: Март 3, 2021
Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well modern organic synthesis, attracting considerable attention from scientific community. Therefore, construction C-Se bond via facile, efficient sustainable strategies to access complex scaffolds simple substrates are appealing hot topic. Visible light can be regarded alternative source energy is associated environmentally-friendly processes. Recently, use visible-light mediated seleno-functionalization has emerged ideal powerful route obtain high-value selenylated products, diminished cost waste. This approach, involving photo-excited substrates/catalyst single-electron transfer (SET) between presence visible been successfully used versatile direct insertion organoselenium moieties activated unactivated C(sp3 )-H, C(sp2 C(sp)-H bonds C-heteroatom bonds. In most cases, ease operation accessibility (LEDs or commercial CFL bulbs) makes this approach more attractive than traditional strategies.
Язык: Английский
Процитировано
44
Catalysts, Год журнала: 2023, Номер 13(7), С. 1056 - 1056
Опубликована: Июнь 30, 2023
Alkenes and their related analogs are ideal starting materials for organic synthesis, the selective difunctionalization of alkenes, which allows simultaneous introduction two neighboring bonds, has gained considerable attention in recent years. In particular, photoredox-catalyzed alkenes also been accomplished, regarded as an increasingly powerful tool synthesis miscellaneous interesting molecular scaffolds environmentally benign economical manner. Several exquisite strategies have developed to facilitate this transformation, such photosensitizer-catalyzed redox reactions, electron donor-acceptor (EDA) complexes-mediated photoreactions, atom transfer radical addition (ATRA) reactions. This literature review briefly describes most key progress on 1,2-difunctionalization various structurally diverse including 1,2-dicarbofunctionalization, 1,2-carboheterofunctionalization, 1,2-diheterofunctionalization, with a special emphasis mechanistic details.
Язык: Английский
Процитировано
22
ACS Catalysis, Год журнала: 2024, Номер 14(7), С. 4847 - 4855
Опубликована: Март 16, 2024
We disclose a copper-photocatalyzed strategy that enables selective access to organic thiocyanates and isothiocyanates using benzylic as ATRA reagents. The electronic nature of the aromatic system is crucial factor defining outcome reaction for forging either kinetic C–S or thermodynamic C–N bonds. Mechanistic investigations support radical pathway initiated by reductive bond cleavage substrates followed divergent inner-/outer-sphere interaction with copper depending on density formed intermediates. developed protocol proceeds high regio- chemoselectivity can also be applied late-stage functionalization bioactive molecules. utility products highlighted their facile conversion several building blocks are relevant synthesis.
Язык: Английский
Процитировано
7
The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(15), С. 10640 - 10653
Опубликована: Июль 13, 2021
A red-light-mediated nPr-DMQA+-catalyzed cascade intramolecular trifluoromethylation and dearomatization of indole derivatives with Umemoto's reagent has been developed. This protocol provides a facile efficient approach for the construction functionalized potentially biologically important CF3-containing 3,3-spirocyclic indolines moderate to high yields excellent diastereoselectivities under mild conditions. The success multiple gram-scale (1 10 g) experiments further highlights robustness practicality this merit employment red light. Mechanistic studies support formation crucial CF3 radical species dearomatized benzyl carbocation intermediate.
Язык: Английский
Процитировано
35