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Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo Cyclopropenes

submitted on 04.01.2019, 05:02 and posted on 04.01.2019, 20:10 by Uyen P. N. Tran, Renè Hommelsheim, Zhen Yang, Claire Empel, Katharina J. Hock, Thanh Vinh Nguyen, Rene Koenigs
The synthesis of trifluoromethylated cyclopropenes is very important for applications in drug discovery and functional materials. In this report, we describe the application of readily available, chiral rhodium(II) catalysts in a highly efficient asymmetric cyclopropenation reaction of fluorinated donor-acceptor diazoalkanes using a broad variety of aliphatic and aromatic alkynes. Further studies highlight the unique reactivity of fluorinated donor-acceptor diazoalkanes in the synthesis of oligo-cyclopropenes. Subsequent C-H functionalization of trifluoromethyl cyclopropenes furnishes densely substituted cyclopropene frameworks and also allows the synthesis of bis-cyclopropenes.


Enantioselective transformations and continuous-flow synthesis of fluorinated diazoalkanes

Deutsche Forschungsgemeinschaft

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Organocatalysis to synthesise organic structures

Australian Research Council

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Email Address of Submitting Author


RWTH Aachen University



ORCID For Submitting Author


Declaration of Conflict of Interest

the authors declare no conflict of interest