2019
DOI: 10.1039/c8qo00985f
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Visible-light-mediated α-phosphorylation of N-aryl tertiary amines through the formation of electron-donor–acceptor complexes: synthetic and mechanistic studies

Abstract: A visible light-mediated photocatalyst-free approach for the oxidative α-CH functionalization of N-aryl tertiary amines with secondary phosphine oxides has been developed.

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Cited by 76 publications
(36 citation statements)
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“…[79] In amechanistically distinct approach, the Lakhdar group reported an a-phosphorylation of N-aryl tertiary amines 29 (Scheme 18). [80] Therein, anilines 29 were identified as suitable substrates to form EDAc omplexes with N-ethoxypyridinium 25,w hich under irradiation with visible light enables PET to liberate the ethoxy radical and amine radical cation. Subsequent a-hydrogen abstraction of the radical cation by the alkoxy radical generates an iminium intermediate,w hich is trapped by ap hosphine oxide 30 to yield aphosphorylated amines 31.…”
Section: N-oxygen-substituted Pyridinium Reagentsmentioning
confidence: 99%
“…[79] In amechanistically distinct approach, the Lakhdar group reported an a-phosphorylation of N-aryl tertiary amines 29 (Scheme 18). [80] Therein, anilines 29 were identified as suitable substrates to form EDAc omplexes with N-ethoxypyridinium 25,w hich under irradiation with visible light enables PET to liberate the ethoxy radical and amine radical cation. Subsequent a-hydrogen abstraction of the radical cation by the alkoxy radical generates an iminium intermediate,w hich is trapped by ap hosphine oxide 30 to yield aphosphorylated amines 31.…”
Section: N-oxygen-substituted Pyridinium Reagentsmentioning
confidence: 99%
“…Afterwards, UV‐Vis experiments suggested the formation of EDA (electron donor‐acceptor) complex between α‐keto acid and 2‐aminothiophenol by clearly shifting the absorption curve of 1 a + 2 a with reference to 1 a and 2 a (Figure ) . The formation of EDA complex was further justified by a change in the physical appearance of the solution of 1 a + 2 a (pale yellow) as compared to that of separate solutions of 1 a and 2 a (colourless) (Figure ).…”
Section: Resultsmentioning
confidence: 96%
“…Im Rahmen eines mechanistisch unterschiedlichen Ansatzes berichtete die Lakhdar‐Gruppe über eine α‐Phosphorylierung von tertiären N ‐Arylaminen 29 (Schema ) . Darin werden Aniline 29 als geeignete Substrate identifiziert, um mit N ‐Ethoxypyridinium 25 EDA‐Komplexe zu bilden, die unter Einstrahlung von sichtbarem Licht PET eingehen und bei der darauf folgenden Fragmentierung ein Ethoxyradikal und Aminoradikalkation freisetzen.…”
Section: Pyridiniumsalze Als Reagenzien Zur üBertragung Funktionellerunclassified