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

• Published in: Chemistry : a European journal Vol. 20; no. 39; pp. 12421 - 12425
• Main Authors: Gwon, Donghyeon, Lee, Donggun, Kim, Jiyu, Park, Sehoon, Chang, Sukbok
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 22.09.2014; WILEY‐VCH Verlag; Wiley
• Subjects: asymmetric induction; Asymmetry; Bearing; Catalysts; Cationic; Chemistry; Chemistry, Multidisciplinary; chirality; CH functionalization; iridium catalysis; phosphine oxides; Physical Sciences; Roads; Science & Technology; Tolerances; asymmetric induction; ASYMMETRIC-SYNTHESIS; CARBON; AZIDES; chirality; ARYLATION; COMPLEXES; ARENES; iridium catalysis; C-H functionalization; phosphine oxides; LIGANDS; BOND ACTIVATION; CH functionalization
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201404151

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).