Zhe-Jie ZhangYing-Feng HsuChia-Chien KaoJYE-SHANE YANG2024-07-162024-07-162024-04-24https://www.scopus.com/record/display.uri?eid=2-s2.0-85191806933&origin=recordpagehttps://scholars.lib.ntu.edu.tw/handle/123456789/719856The previously eight-step synthesis of bis(arylamino)pentiptycenes (2) from pentiptycene quinone (1) can now be achieved in a single step with 18–90% yields through TiCl4-DABCO assisted reductive amination with anilines. Both the dual amination of 1 and the in situ reduction of quinone diimines are unprecedented. The π system of 2 can be further expanded, including the formation of bis(diarylamino)pentiptycenes. This work also provides mechanistic insights into the challenges encountered in the dual reductive amination of 1 with other amines.enjournal article10.1021/acs.orglett.4c00939