title: Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C-O or C-N Bond Cleavage.
abstract: Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C-O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)2] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C-N bond cleavage in the presence of a [Pd(PPh3)2Cl2] catalyst. These methods enable selective sequential functionalizations of arenes having both C-N and C-O bonds in one pot.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Ze-Kun
authors.initials: ZK
authors.lastname: Yang
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Dong-Yu
authors.initials: DY
authors.lastname: Wang
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Minami
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Ogawa
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Ozaki
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Tatsuo
authors.initials: T
authors.lastname: Saito
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan. chaowang@mol.f.u-tokyo.ac.jp, chaowang@riken.jp.|Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, RIKEN Elements Chemistry Laboratory, 2-1 Hirosawa, Wako-shi, Saitama-ken, 351-0198, Japan. chaowang@mol.f.u-tokyo.ac.jp, chaowang@riken.jp.
authors.forename: Chao
authors.identifier: http://orcid.org/0000-0002-9165-7758
authors.initials: C
authors.lastname: Wang
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to, 113-0033, Japan. uchiyama@mol.f.u-tokyo.ac.jp, uchi_yama@riken.jp.|Advanced Elements Chemistry Research Team, RIKEN Center for Sustainable Resource Science, RIKEN Elements Chemistry Laboratory, 2-1 Hirosawa, Wako-shi, Saitama-ken, 351-0198, Japan. uchiyama@mol.f.u-tokyo.ac.jp, uchi_yama@riken.jp.
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
keywords: ammonium salt; cross-coupling; ether; organolithium; transition metal catalyst