A Sc(OTf) catalyzed dehydrogenative reaction of electron-rich (hetero)aryl nucleophiles with 9-aryl-fluoren-9-ols

A highly efficient dehydrogenative reaction of a series of nucleophiles with 9-aryl-fluoren-9-ols has been realized by using only 2 mol% of Sc(OTf) 3 as a catalyst. The corresponding indole-containing 9,9-diarylfluorenes were obtained in up to 99% yield as well as other electron-rich (hetero)arene a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-11, Vol.17 (44), p.9615-9619
Main Authors: Zhou, Chen, Hu, Chen, Hong, Gang, He, Yuchen, Tang, Zhicong, Wang, Limin
Format: Article
Language:English
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Summary:A highly efficient dehydrogenative reaction of a series of nucleophiles with 9-aryl-fluoren-9-ols has been realized by using only 2 mol% of Sc(OTf) 3 as a catalyst. The corresponding indole-containing 9,9-diarylfluorenes were obtained in up to 99% yield as well as other electron-rich (hetero)arene adducts. The protocol exhibits high selectivity, mild reaction conditions and good substrate compatibility (32 examples). This protocol is further highlighted by its applications in the construction of potential electroluminescent materials. New pyrenyl substituted 9,9-diarylfluorene with nonplanar conformations, high fluorescence quantum yield and excellent thermal and morphological stability was synthesized by our current protocol.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02138h