Cross‐Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C−O or C−N Bond Cleavage. Issue 44 (15th September 2016)

• Record Type: Journal Article
• Authors: Yang, Ze‐Kun; Wang, Dong‐Yu; Minami, Hiroki; Ogawa, Hiroyuki; Ozaki, Takashi; Saito, Tatsuo; Miyamoto, Kazunori; Wang, Chao; Uchiyama, Masanobu
• Is Part Of: Chemistry. Volume 22:Issue 44(2016)
• Page Start: 15693
• Page End: 15699
• Publication Date: 2016-09-15
• Subjects: ammonium salt -- cross-coupling -- ether -- organolithium -- transition metal catalyst; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201603436
• Languages: English
• ISSNs: 0947-6539

Abstract

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 )2 Cl2 ] catalyst. These methods enable selective sequential functionalizations of arenes having both C−N and C−O bonds in one pot. Abstract : Cut and paste ! Various aryl‐, alkenyl‐, and/or alkyllithium species smoothly reacted with aryl and/or alkyl ethers with cleavage of the inert C−O bond, catalyzed by an Ni catalyst. The coupling reaction between the aryllithium reagents and aryl ammonium salts also proceeded under mild conditions by a C−N bond cleavage in the presence of a Pd catalyst. These methods enable selective and sequential functionalizations of arenes having both C−N and C−O bonds, in one pot.