Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3341 - 3346
Published: Jan. 1, 2023
Herein, we describe a novel and efficient photo-redox catalytic difluorinated ester radical addition/defluoroalkylation coupling reaction between trifluoroacetic acid derivatives α-trifluoromethyl alkenes.
Language: Английский
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(17), P. 6733 - 6738
Published: Jan. 1, 2023
A metal free, visible-light driven α-C(sp 3 )−H gem-difluoroallylation of glycine derivatives with CF -alkenes and 1,3-enynes is presented under redox-neutral conditions good yields excellent functional group compatibility.
Language: Английский
Citations
28
Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3909 - 3915
Published: Jan. 1, 2023
Visible light-induced highly efficient synthesis of 1,3-disubstituted bicyclo[1.1.1]pentane with mild conditions, high atom economy, and superior functional group tolerance.
Language: Английский
Citations
26
Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1393 - 1398
Published: Feb. 12, 2024
We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.
Language: Английский
Citations
10
Chemical Communications, Journal Year: 2023, Volume and Issue: 59(25), P. 3707 - 3710
Published: Jan. 1, 2023
Radical defluorinative functionalization of α-trifluoromethyl styrenes represents an effective way toward gem-difluoroalkenes. There are general interests in developing novel synthetic protocols for with various types radicals. However, reports on the preparation gem-difluoro allylsulfones via S-centered radical pathway limited. Herein, we developed a photo/nickel dual-catalyzed sulfonylation that rapidly and reliably synthesizes allylsulfones. The merit this protocol is exhibited by its mild conditions wide scope, thus providing strategy sulfonyl participating coupling.
Language: Английский
Citations
17
ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8252 - 8260
Published: May 13, 2024
Due to their appealing physiological attributes, tertiary aliphatic amines are pervasive in a myriad of biologically active molecules. In particular, featuring homoallylic substituents serve as versatile synthetic building blocks. Therefore, there is growing demand for the development practical and modular methods rapid assembly sp3-rich complex from readily accessible chemical feedstock. Here, we disclose multicomponent, reductive photocatalytic protocol that merges secondary alkylamines, carbonyl compounds, fluoroalkyl-substituted alkenes, yielding fluorinated homoallylamines. This defluorinative aminoalkylation involves addition alkyl-substituted α-amino radicals, generated reduction situ-generated iminium ions by photocatalyst, alkenes subsequent fluoride elimination, reliably furnishing gem-difluoroalkene monofluoroalkene motifs not easily through alternative methods. Utility method was demonstrated its broad functional group compatibility, derivatization synthesis drug analogues.
Language: Английский
Citations
8
Chemical Science, Journal Year: 2024, Volume and Issue: 15(33), P. 13466 - 13474
Published: Jan. 1, 2024
Herein, non-donor acceptor-type naphthocarbazole derivatives (NCs), possessing fine-tuned redox properties, were reported as efficient photoredox catalyst for reductive transformation under mild and environmentally benign reaction conditions.
Language: Английский
Citations
7
Organic Letters, Journal Year: 2022, Volume and Issue: 24(37), P. 6834 - 6838
Published: Sept. 8, 2022
A visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to γ-oximino esters under mild conditions. Significantly, this transformation not only shows the good compatibility nucleophilic electrophilic but also displays generating alkyl radicals that preferred addition over nitroso radicals.
Language: Английский
Citations
28
Organic Letters, Journal Year: 2022, Volume and Issue: 24(38), P. 7047 - 7051
Published: Sept. 19, 2022
Commercially available CF2Br2 has been used as a convenient source for the rapid and reliable incorporation of gem-difluorovinyl motif into an allene framework via N-heterocyclic carbene catalyzed difluoroolefination 1,3-enynes. The reaction proceeds through cascade three-component radical relay/elimination process. This protocol is distinguished by its mild conditions, readily accessible starting materials, wide substrate scope, ease late-stage functionalization, thus unlocking untraditional strategy to construct new class functionalized allenes.
Language: Английский
Citations
28
Chemical Science, Journal Year: 2022, Volume and Issue: 13(44), P. 13141 - 13146
Published: Jan. 1, 2022
Photoexcitation of the azodicarboxylates results in a radical addition reaction with diazoalkanes and formation an azomethine ylide to allow for dipolar cycloaddition nitriles give 1,2,4-triazole.
Language: Английский
Citations
26
Organic Letters, Journal Year: 2022, Volume and Issue: 24(48), P. 8753 - 8758
Published: Nov. 28, 2022
The unprecedented photochemical late-stage defluorinative gem-difluoroallylation of aryl sulfonium salts, which are formed site-selectively by direct C(sp2)─H functionalization, is herein disclosed. This method distinguished its mild reaction conditions, wide scope, and excellent site-selectivity. As showcase examples, a Flurbiprofen Pyriproxyfen derivatives could be late stage gem-difluoroallylated with high yields. Experimental computational investigations were conducted.
Language: Английский
Citations
25