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Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo‐Cyclopropenes
Author(s) -
Tran Uyen P. N.,
Hommelsheim Renè,
Yang Zhen,
Empel Claire,
Hock Katharina J.,
Nguyen Thanh V.,
Koenigs René M.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904680
Subject(s) - cyclopropene , trifluoromethyl , chemistry , catalysis , combinatorial chemistry , acceptor , reactivity (psychology) , organic chemistry , medicine , alkyl , physics , alternative medicine , pathology , condensed matter physics
The synthesis of trifluoromethylated cyclopropenes is often associated with important applications in drug discovery and functional materials. In this report, we describe the use of readily available chiral rhodium(II) catalysts for a highly efficient asymmetric cyclopropenation reaction of fluorinated donor–acceptor diazoalkanes with 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 alternative synthesis of bis‐cyclopropenes.