2003
DOI: 10.1021/jo020696+
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N-Arylation of Aziridines

Abstract: A range of N-arylaziridines were prepared by the palladium or copper catalyzed amination reaction between N-H aziridines and aryl bromides or arylboronic acids. These results showcase the synthetic utility of metal-bound aziridine species in nitrogen transfer processes.

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Cited by 65 publications
(29 citation statements)
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References 22 publications
(28 reference statements)
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“…Both palladium-and copper-catalyzed routes were successful with a range of boronic acids (Scheme 27). [54] Scheme 25. Key step: Boronic acid (1.5 equiv), Cu(OAc) 2 (5-20 mol %), myristic acid (10-40 mol %), air, 2,6-lutidine, toluene, room temperature, vigorous stirring, 24 h. The need for better synthetic access to 129 led Guy and co-workers to explore a copper-mediated S-arylation of thiols (cysteine derivative) with phenylboronic acids in a formal synthesis of nelfinavir.…”
Section: Methodsmentioning
confidence: 99%
“…Both palladium-and copper-catalyzed routes were successful with a range of boronic acids (Scheme 27). [54] Scheme 25. Key step: Boronic acid (1.5 equiv), Cu(OAc) 2 (5-20 mol %), myristic acid (10-40 mol %), air, 2,6-lutidine, toluene, room temperature, vigorous stirring, 24 h. The need for better synthetic access to 129 led Guy and co-workers to explore a copper-mediated S-arylation of thiols (cysteine derivative) with phenylboronic acids in a formal synthesis of nelfinavir.…”
Section: Methodsmentioning
confidence: 99%
“…Es muss angemerkt werden, dass aufgrund der Bildung von Diphenylamin als Nebenprodukt geringere Ausbeuten erhalten wurden. Später haben Sasaki und Mitarbeiter gezeigt, dass ähnliche Reaktionsbedingungen auch mit Aziridinen für die Synthese von N‐Arylaziridinen kompatibel sind . Einige Jahre später haben Batey und Quach die ligand‐ und basenfreie Cu‐katalysierte Kreuzkupplung von Organoborverbindungen mit aliphatischen Aminen und Anilinen in Gegenwart von 4‐Å‐Molekularsieb und Sauerstoff beschrieben (Nr.…”
Section: Cu‐katalysierte Kreuzkupplungen Von (Hetero)arylboronaten MIunclassified
“…The same aziridine undergoes smooth palladiumcatalyzed allylation with prenyl acetate, whereby the electrophile is captured at the more substituted terminus (route b), although this regiochemistry is substratedependent [189]. N-Arylation is also possible using a palladium/BINAP protocol (route c), in which aryl bromides and arylboronic acids act as suitable reaction partners [190]. Many other protocols exist in which unprotected aziridines function as nucleophiles, including alkylations using epoxides [191] or alkyl bromides [192] as electrophiles.…”
Section: N-elaboration Reactionsmentioning
confidence: 99%