The previously eight-step synthesis of bis(arylamino)pentiptycenes () from pentiptycene quinone () can now be achieved in a single step with 18-90% yields through TiCl-DABCO assisted reductive amination with anilines. Both the dual amination of and the reduction of quinone diimines are unprecedented. The π system of 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 with other amines.
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| http://dx.doi.org/10.1021/acs.orglett.4c00939 | DOI Listing |
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