Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 26, Issue 8, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201179
Keywords
benzoic acid; C-H activation; Fujiwara-Moritani; traceless directing group; unactivated alkene
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Here 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. The new C-C bond is formed to the C2 of the terminal olefin, in contrast to similar reported transformations. Initial mixtures of exo- and endo-double bond isomers can be efficiently isomerized to the more stable endo-products.
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.
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