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Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo-Cyclopropenes.

ABSTRACT: 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.

SUBMITTER: Tran UPN

PROVIDER: S-EPMC7028152 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo-Cyclopropenes.

Tran Uyen P N UPN Hommelsheim Renè R Yang Zhen Z Empel Claire C Hock Katharina J KJ Nguyen Thanh V TV Koenigs René M RM

Chemistry (Weinheim an der Bergstrasse, Germany) 20200120 6

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 o ...[more]

PMID: 31617620

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