Iron-catalyzed ortho-allylation of aromatic carboxamides with allyl ethers.
Arenes possessing an N-(quinolin-8-yl)amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 °C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in γ-selective fashion.
Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Sobi
S
Asako
Laurean
L
Ilies
Eiichi
E
Nakamura
D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007501:Iron / Q000737:chemistry*; D010647:Phenyl Ethers / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*
D000498:Allyl Compounds; D000577:Amides; D010647:Phenyl Ethers; D010720:Phosphines; D011804:Quinolines; C076695:phenyl allyl ether; D007501:Iron; C044646:phosphine