title: Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air.
abstract: Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.
authors.affiliation: Research Institute for Interdisciplinary Science, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Iwasaki
authors.affiliation: Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Natsumi
authors.initials: N
authors.lastname: Miki
authors.affiliation: Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Tsuchiya
authors.affiliation: Department of Chemistry, Aichi University of Education , Igaya, Kariya 448-8542, Japan.
authors.forename: Kiyohiko
authors.initials: K
authors.lastname: Nakajima
authors.affiliation: Research Institute for Interdisciplinary Science, Okayama University , 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan.
authors.forename: Yasushi
authors.identifier: 0000-0001-5409-4207
authors.initials: Y
authors.lastname: Nishihara