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Title: Rhodium-catalysed C(sp2)–C(sp2) bond formation via C–H/C–F activation
Authors: Tian, Panpan
Feng, Chao
Loh, Teck-Peng
Keywords: Design, Synthesis and Processing
Issue Date: 2015
Source: Tian, P., Feng, C., & Loh, T.-P. (2015). Rhodium-catalysed C(sp2)–C(sp2) bond formation via C–H/C–F activation. Nature Communications, 6, 7472-. doi:10.1038/ncomms8472
Series/Report no.: Nature Communications
Abstract: Fluoroalkenes represent a class of privileged structural motifs, which found widespread use in medicinal chemistry. However, the synthetic access to fluoroalkenes was much underdeveloped with previous reported methods suffering from either low step economy or harsh reaction conditions. Here we present a RhIII-catalysed tandem C–H/C–F activation for the synthesis of (hetero)arylated monofluoroalkenes. The use of readily available gem-difluoroalkenes as electrophiles provides a highly efficient and operationally simple method for the introduction of α-fluoroalkenyl motifs onto (hetero)arenes under oxidant-free conditions. Furthermore, the employment of alcoholic solvent and the in-situ generated hydrogen fluoride are found to be beneficial in this transformation, indicating the possibility of the involvement of hydrogen bond activation mode with regards to the C–F bond cleavage step.
Rights: © 2015 Macmillan Publishers Limited. This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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