title: Ruthenium-Catalyzed Monoalkenylation of Aromatic Ketones by Cleavage of Carbon-Heteroatom Bonds with Unconventional Chemoselectivity.
abstract: Ruthenium-catalyzed selective monoalkenylation of ortho C-O or C-N bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon-heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved.
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 (Japan).
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kondo
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 (Japan).
authors.forename: Nana
authors.initials: N
authors.lastname: Akiba
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 (Japan).
authors.forename: Takuya
authors.initials: T
authors.lastname: Kochi
authors.affiliation: Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 (Japan). kakiuchi@chem.keio.ac.jp.|JST, ACT-C, Kawaguchi, Saitama, 332-0012 (Japan). kakiuchi@chem.keio.ac.jp.
authors.forename: Fumitoshi
authors.initials: F
authors.lastname: Kakiuchi
keywords: boron; chemoselectivity; ruthenium; substituent effects; synthetic methods