Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation

• Published in: Tetrahedron Vol. 64; no. 29; pp. 6824 - 6830
• Main Authors: Boebel, Timothy A., Hartwig, John F.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 14.07.2008; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; IRIDIUM-CATALYZED BORYLATION; ASYMMETRIC-SYNTHESIS; ARYLBORONIC ESTERS; IMINES; COUPLING REACTION; ALPHA-AMINO-ACIDS; N-TERT-BUTANESULFINYL; ORGANOLITHIUM REAGENTS; ROOM-TEMPERATURE REACTIONS; C-H BONDS

A two-step conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides is described. In this procedure, arenes are converted to aryl boronic esters by iridium-catalyzed borylation, and the aryl boronic esters are converted to enantioenriched amines by subsequent rhodium-cata...