Pourkaveh, R., Podewitz, M., & Schnürch, M. (2023). A Fujiwara-Moritani-type alkenylation using a traceless directing group strategy: a rare example of C-C bond formation towards the C2-carbon of terminal alkenes. European Journal of Organic Chemistry, 26(8), Article e202201179. https://doi.org/10.1002/ejoc.202201179
E163 - Institut für Angewandte Synthesechemie E163-03 - Forschungsbereich Organische und Biologische Chemie E163-03-4 - Forschungsgruppe Bioorganische Synthesechemie E165-03 - Forschungsbereich Theoretische Chemie E165 - Institut für Materialchemie E165-03-1 - Forschungsgruppe Theoretische Materialchemie E150 - Fakultät für Technische Chemie
-
Journal:
European Journal of Organic Chemistry
-
ISSN:
1434-193X
-
Date (published):
17-Feb-2023
-
Number of Pages:
6
-
Publisher:
Wiley
-
Peer reviewed:
Yes
-
Keywords:
benzoic acid; C-H Activation; olefination
en
Abstract:
Herein we report, a rhodium-catalyzed Fujiwara-Moritani-type reaction of unactivated terminal alkenes and benzoic acid derivatives bearing electron donating residues under mild conditions. The acid functionality acts as a traceless directing group delivering products alkenylated in meta-position to the electron donating substituent in contrast to the usually obtained ortho- and para-substitution in Friedel-Crafts-type reactions. Remarkably, the new C−C bond is formed to the C2 of the terminal olefin, in contrast to similar reported transformations. Initially formed mixtures of exo- and endo-double bond isomers can be efficiently isomerized to the more stable endo-products.
en
Research facilities:
Zentrum für Kernspinresonanzspektroskopie
-
Project title:
Substitution von gasförmigen Reagenzien durch Feststoffe: P 33064-N (FWF Fonds zur Förderung der wissenschaftlichen Forschung (FWF))
CC BY 4.0
