One-Pot Synthesis of Bis(arylamino)pentiptycenes by TiCl4‑DABCO Assisted Reductive Amination of Pentiptycene Quinone

The 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 ar...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 17; pp. 3547 - 3551
Main Authors Zhang, Zhe-Jie, Hsu, Ying-Feng, Kao, Chia-Chien, Yang, Jye-Shane
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
POLYMERS
DERIVATIVES
POLYANILINE
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Summary:The 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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00939