Herein, we report the use of a bromine atom as a masking group for the synthesis atropisomeric diarylamines via organocatalytic N-arylation of 7-bromoindolines. The bromine atom acts as a bulky group to temporarily stabilize the configuration by steric hindrance. Upon unmasking, less sterically hindered diarylamines are obtained, with configurational stability potentially maintained through intramolecular hydrogen bonding. Moreover, the gram-scale reaction and post-modifications of the axially chiral diarylamines demonstrated the utility of this protocol. Thermal racemization experiments combi...
