2023
DOI: 10.1021/acs.orglett.2c04027
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Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines

Abstract: A solvent (2,2,2-trifluoroethanol (TFE) vs ethyl alcohol (EtOH)) switched synthesis of quinolines and pyridines is illustrated from (E)-2-(1,3-diphenylallylidene)­malononitriles via a Pd­(II)-catalyzed photochemical process. The active catalyst [L2Pd­(0)] generated serves as an exogenous photosensitizer. The process offers predominantly Z-alkenylated quinolines and pyridines in TFE and EtOH, respectively. Furthermore, large-scale synthesis and a few interesting post-synthetic modifications have been demonstrat… Show more

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Cited by 8 publications
(4 citation statements)
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“…This synthetic protocol possesses broad scope and more than 70 derivatives were synthesized along with late-stage functionalizations of agrochemicals and drugs. In a model reaction 4-bromobenzonitrile (19) was used toward the C(sp 3 )-H bond arylation of N,N-dimethyl acetamide (DMA) (20) as both solvent and C-H precursor. At first the optimization of various reaction parameters was carried out and after that, a library of compounds was synthesized.…”
Section: Semi-heterogeneous Dual Carbon Nitride Metallo-photoredox Ca...mentioning
confidence: 99%
See 1 more Smart Citation
“…This synthetic protocol possesses broad scope and more than 70 derivatives were synthesized along with late-stage functionalizations of agrochemicals and drugs. In a model reaction 4-bromobenzonitrile (19) was used toward the C(sp 3 )-H bond arylation of N,N-dimethyl acetamide (DMA) (20) as both solvent and C-H precursor. At first the optimization of various reaction parameters was carried out and after that, a library of compounds was synthesized.…”
Section: Semi-heterogeneous Dual Carbon Nitride Metallo-photoredox Ca...mentioning
confidence: 99%
“…17 Photochemically, a wide range of complex synthetic conversions have been developed in recent years. [18][19][20][21][22][23][24] In contrast to conventional catalysis, photocatalysis exploits the formation of reactive intermediates by photo-induced electron, atom, or energy transfer processes. 25,26 Commonly used photocatalysts (PCs) are mainly conjugated systems that consist of aromatic chromophores, inorganic clusters, organic dyes, and transition metal complexes.…”
mentioning
confidence: 99%
“…We have also successfully developed the synthesis of 3-cyanopyridines from γ-ketodinitriles and dicyanodienes under visible light irradiation without using any exogenous photosensitizer [Scheme 1(iii)]. 10…”
mentioning
confidence: 99%
“…From our continuous contributions in nitrile-triggered reactions to access various heterocycles 10,13 and taking cues from the previous literature reports, we now envision the synthesis of tetrasubstituted pyridines under metal- and photocatalyst-free conditions. Therefore, herein we disclose a visible-light-induced synthesis of thio-functionalized pyridine from ( E )-2-(1,3-diphenylallylidene)malononitrile ( 1 ) and thiophenol ( a ) via the formation of an electron–donor–acceptor (EDA) complex.…”
mentioning
confidence: 99%