Synlett 2022; 33(18): 1826-1830
DOI: 10.1055/a-1770-1078
cluster
Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

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

Shulei Pan
a   School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China
b   West China Biopharmaceutical Research Institute, West China Hospital, Sichuan University, Chengdu, Sichuan 610041, P. R. of China
,
Qiongqiong Zhu
a   School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China
,
Yanghui Zhang
a   School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China
› Institutsangaben
The work was supported by the National Natural Science Foundation of China (No. 21971196) and the Science and Technology Commission of Shanghai Municipality (19DZ2271500).


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(sp2)–C(sp3) bonds through reaction with CH2Br2. The reaction tolerates various functional groups, permitting easy access to a range of fluorene derivatives.

Supporting Information



Publikationsverlauf

Eingereicht: 16. Januar 2022

Angenommen nach Revision: 11. Februar 2022

Accepted Manuscript online:
11. Februar 2022

Artikel online veröffentlicht:
10. März 2022

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