Palladium-Catalyzed Coupling of Biphenyl-2-yl Trifluoromethanesulfonates with Dibromomethane to Access Fluorenes

Abstract A facile and efficient method has been developed for the synthesis of fluorenes by Pd-catalyzed C–H alkylation of biphenyl-2-yl trifluoromethanesulfonates. The trifluoromethanesulfonates are more readily available and more environmentally benign than biphenyl iodides, and are advantageous s...

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Bibliographic Details
Published in:Synlett 2022-11, Vol.33 (18), p.1826-1830
Main Authors: Pan, Shulei, Zhu, Qiongqiong, Zhang, Yanghui
Format: Article
Language:English
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cluster
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Summary:Abstract A facile and efficient method has been developed for the synthesis of fluorenes by Pd-catalyzed C–H alkylation of biphenyl-2-yl trifluoromethanesulfonates. The trifluoromethanesulfonates are more readily available and more environmentally benign than biphenyl iodides, and are advantageous substrates for traceless directing-group-assisted C–H activation. The reaction generates C,C-palladacycles as the key intermediates that form two C(sp 2 )–C(sp 3 ) bonds through reaction with CH 2 Br 2 . The reaction tolerates various functional groups, permitting easy access to a range of fluorene derivatives.
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1770-1078