Difluorocarbene Addition to Alkenes and Alkynes in Continuous Flow.
The first in-flow difluorocarbene generation and addition to alkenes and alkynes is reported. The application of continuous flow technology allowed for the controlled generation of difluorocarbene from TMSCF3 and a catalytic quantity of NaI. The in situ generated electrophilic carbene reacts smoothly with a broad range of alkenes and alkynes, allowing the synthesis of the corresponding difluorocyclopropanes and difluorocyclopropenes. The reaction is complete within a 10 min residence time at high reaction concentrations. With a production flow rate of 1 mmol/min, continuous flow chemistry enables scale up of this process in a green, atom-economic, and safe manner.
Université de Montréal , Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, P.O. Box 6128, Station Downtown, Québec, Canada H3C 3J7.
Pauline
P
Rullière
Université de Montréal , Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, P.O. Box 6128, Station Downtown, Québec, Canada H3C 3J7.
Patrick
P
Cyr
Université de Montréal , Centre in Green Chemistry and Catalysis, Department of Chemistry, Faculty of Arts and Science, P.O. Box 6128, Station Downtown, Québec, Canada H3C 3J7.
André B
AB
Charette