Journal of the American Chemical Society
by Yusuke Masuda, Naoki Ishida and Masahiro Murakami
/
1d
// keep unread
// hide
// preview
C–C bond forming carboxylation reactions of organic molecules with carbon dioxide (CO2) have gained considerable attention in organic synthesis.(1) Most conventional methods including Grignard reactions and transition metal catalysis use stoichiometric amounts of reducing agents or bases.(2-4) The major driving force of these carboxylation reactions derives from the chemical reagents. Alternatively, electro-(5) or photo-assisted(6) reductive carboxylation reactions have been devised. Electron donors like triethylamine were used as the sacrificial reducing agents in most cases. Herein, we report a unique and clean carboxylation reaction that uses no sacrificial reagent but light energy as the driving force; simply upon UV irradiation of a DMSO solution of o-alkylphenyl ketones, CO2 is efficiently incorporated to produce o-acylphenylacetic acids.
http://pubs.acs.org/doi/10.1021/jacs.5b10032
http://pubs.acs.org/doi/pdf/10.1021/jacs.5b10032
Visit Website
C–C bond forming carboxylation reactions of organic molecules with carbon dioxide (CO2) have gained considerable attention in organic synthesis.(1) Most conventional methods including Grignard reactions and transition metal catalysis use stoichiometric amounts of reducing agents or bases.(2-4) The major driving force of these carboxylation reactions derives from the chemical reagents. Alternatively, electro-(5) or photo-assisted(6) reductive carboxylation reactions have been devised. Electron donors like triethylamine were used as the sacrificial reducing agents in most cases. Herein, we report a unique and clean carboxylation reaction that uses no sacrificial reagent but light energy as the driving force; simply upon UV irradiation of a DMSO solution of o-alkylphenyl ketones, CO2 is efficiently incorporated to produce o-acylphenylacetic acids.
http://pubs.acs.org/doi/10.1021/jacs.5b10032
http://pubs.acs.org/doi/pdf/10.1021/jacs.5b10032
コメント