Iridium(III)-Catalyzed CH Amidation of Arylphosphoryls Leading to a P-Stereogenic Center

Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving...

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Veröffentlicht in:Chemistry : a European journal 2014-09, Vol.20 (39), p.12421-12425
Hauptverfasser: Gwon, Donghyeon, Lee, Donggun, Kim, Jiyu, Park, Sehoon, Chang, Sukbok
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Sprache:eng
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Zusammenfassung:Direct CH amidation of arylphosphoryl compounds has been developed by using an IrIII catalyst system under mild conditions. A wide range of substrates could be employed with high functional‐group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P‐chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de). A road to­ P‐chirality: A cationic [IrIII(Cp*)] complex catalyzes the direct CH amidation of diarylphosphorus compounds bearing a chiral auxiliary to allow for a straightforward route to optically pure P‐chiral compounds (see scheme; Cp*=1,2,3,4,5‐pentamethylcyclopentadiene).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201404151