Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(11), С. 3012 - 3021
Опубликована: Янв. 1, 2022
An efficient strategy for the divergent synthesis of N , -disubstituted hydrazides and their bromides is reported through photoredox-catalytic cross-dehydrogenative coupling hydrazines aldehydes.
Язык: Английский
Organic Letters, Год журнала: 2021, Номер 23(8), С. 2976 - 2980
Опубликована: Март 29, 2021
A general and metal-free visible-light-induced decarboxylative arylation procedure at room temperature was described for the construction of acylated heterocyclic derivatives, such as benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones, aroylazaspiro[4.5]trienones, thioflavones, so on. This practical conducted by using 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) a photocatalyst under mild conditions, which avoided use an additional base, traditional heating, metal reagents.
Язык: Английский
Процитировано
125
ACS Sustainable Chemistry & Engineering, Год журнала: 2021, Номер 9(12), С. 4296 - 4323
Опубликована: Март 16, 2021
Pollutants from industry and chemical laboratories have harmful effects on human health the environment. Concerns about this problem led to development of more versatile sustainable protocols based principles green chemistry. One these innovative approaches is carry out reactions under visible-light sources without photocatalysts. This benign, simple, cost-effective method, inspired by nature, could be a suitable alternative some classical methods, change harsh reaction conditions into milder ones. In Perspective, we outlined results catalyst-free organic further encourage researchers in promising field. The proposed mechanisms generation an electron donor–acceptor complex (EDA) single-electron transfer (SET) pathway were discussed.
Язык: Английский
Процитировано
90
International Journal of Biological Macromolecules, Год журнала: 2021, Номер 185, С. 890 - 906
Опубликована: Июнь 29, 2021
Язык: Английский
Процитировано
85
Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(11), С. 2678 - 2722
Опубликована: Март 31, 2021
Abstract Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic derivatives in decarboxylative couplings has proven be a valuable tool for construction C−C C‐heteroatom bonds. This synthetic strategy provides complementary bond disconnection traditional cross‐coupling methods. In this review, we provide comprehensive overview decarboxylation‐initiated intermolecular formation, outlining several main mechanistic concepts combined with early examples highlighting achievements made past decade until January 2021. these reactions, undergo initial decarboxylation then react other heteroatom electrophiles nucleophiles, thus replacing carboxylate group prevalent functionality. magnified image
Язык: Английский
Процитировано
83
Organic Letters, Год журнала: 2024, Номер 26(2), С. 498 - 502
Опубликована: Янв. 9, 2024
The convenient and precise preparation of N,N′-diarylhydrazides, especially from readily available raw materials, remains highly challenging. Here, a photoredox catalytic phosphine-mediated deoxygenative hydroacylation azobenzenes with abundant carboxylic acids has been developed. With Ir[dF(CF3)ppy]2(dtbbpy)PF6 as the photocatalyst, reactions proceeded smoothly in presence PPh3 under visible light irradiation, delivering various N,N′-diarylhydrazides up to 92% yields. Mechanistic studies revealed that reaction proceeds via catalysis phosphoranyl-radical-mediated C–O bond cleavage acids.
Язык: Английский
Процитировано
14
Chemical Society Reviews, Год журнала: 2024, Номер 53(10), С. 4926 - 4975
Опубликована: Янв. 1, 2024
In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.
Язык: Английский
Процитировано
13
Green Chemistry, Год журнала: 2021, Номер 23(16), С. 5806 - 5811
Опубликована: Янв. 1, 2021
Direct synthesis of 1,2,4-triazolidines have been readily achieved by the visible-light-promoted reaction N -aryl glycines and azobenzenes under mild conditions.
Язык: Английский
Процитировано
42
Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(11), С. 1230 - 1236
Опубликована: Фев. 5, 2024
Comprehensive Summary A visible‐light‐enabled, photocatalyst‐free hydroacylation reaction of azodicarboxylic acid derivatives was described. This radical conjugate addition (RCA) protocol relied on the dual role 4‐acyl‐1,4‐dihydropyridine (acyl‐DHP) reagents that besides being as reservoirs, they also enabled conversion adducts to anion intermediates via reduction. Under “catalyst‐oxidant‐additive free” conditions, a wide range structurally different acyl hydrazide products were readily obtained in 56%—99% yields. The utility this transformation further demonstrated by scale‐up synthesis and downstream derivatization.
Язык: Английский
Процитировано
8
Organic Letters, Год журнала: 2024, Номер 26(10), С. 2039 - 2044
Опубликована: Март 4, 2024
We report the synthesis of acyl hydrazides from acylsilanes in presence visible light without aid additives or transition metals. Acylsilanes underwent [1,2]-Brook rearrangement to generate nucleophilic siloxycarbenes which on further addition N═N azodicarboxylates produced hydrazides. Control experiments indicate that reaction proceeds through singlet carbene intermediate. Transformation hydrazide functionality other functional groups was demonstrated, including drug candidate Moclobemide.
Язык: Английский
Процитировано
8
Organic Letters, Год журнала: 2022, Номер 24(7), С. 1530 - 1535
Опубликована: Фев. 14, 2022
A visible-light-promoted aerobic oxyphosphorylation of α-diazoesters and H-phosphine oxides has been developed. Using air as the oxygen source, reaction proceeded smoothly at room temperature under blue-light irradiation. The α-diazoesters, molecular oxygen, are conveniently incorporated into a C-O-P(O) unit in one step. preliminary mechanistic studies indicated that light-triggered radical process is involved. developed strategy shows unrevealed reactivity diazo compounds with potential value synthetic applications.
Язык: Английский
Процитировано
24