Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines**
2022; Wiley; Volume: 29; Issue: 6 Linguagem: Inglês
10.1002/chem.202203269
ISSN1521-3765
AutoresRaphael F. Fritsche, Tristan Schuh, Olga Kataeva, Hans‐Joachim Knölker,
Tópico(s)Molecular spectroscopy and chirality
ResumoWe describe an iron-catalyzed asymmetric oxidative C-C coupling of diarylamines which proceeds at room temperature with air as final oxidant. Using hexadecafluorophthalocyanine-iron(II) as catalyst in the presence of catalytic amounts of an axially chiral biaryl phosphoric acid, the resulting chiral 2,2'-diamino-1,1'-biaryls are obtained in up to 90 % ee as confirmed by chiral HPLC. A detailed mechanism has been proposed with a radical cation-chiral phosphate ion pair as key intermediate leading to the observed asymmetric induction.
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