Double strain-release enables formal C-O/C-F and C-N/C-F ring-opening metathesis.

ABSTRACT: Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved in double-bond metathesis, like olefin metathesis and carbonyl metathesis, single-bond metathesis has received less attention in the past decade. Herein, we describe the first C(sp³)-O/C(sp³)-F bond formal cross metathesis reaction between gem-difluorinated cyclopropanes (gem-DFCPs) and epoxides under rhodium catalysis. The reaction involves the formation of a highly electrophilic fluoroallyl rhodium intermediate, which is capable of reacting with the oxygen atom in epoxides as weak nucleophiles followed by C-F bond reconstruction. The use of two strained ring substrates is the key to the success of the formal cross metathesis, in which

SUBMITTER: Zhu Y 

PROVIDER: S-EPMC11310891 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature