29304-66-3Relevant academic research and scientific papers
Nickel-Catalyzed Kumada Coupling of Boc-Activated Aromatic Amines via Nondirected Selective Aryl C-N Bond Cleavage
Zhang, Zheng-Bing,Ji, Chong-Lei,Yang, Ce,Chen, Jie,Hong, Xin,Xia, Ji-Bao
, p. 1226 - 1231 (2019/02/14)
A nickel-catalyzed Kumada coupling of aniline derivatives was developed by selective cleavage of aryl C-N bonds under mild reaction conditions. Without preinstallation of an ortho directing group on anilines, the cross-coupling reactions of Boc-protected aromatic amines with aryl Grignard reagents afforded unsymmetric biaryls. Mechanistic studies by DFT calculations revealed that the nickel-mediated C-N bond cleavage is the rate-limiting step.
One-Pot Photomediated Giese Reaction/Friedel-Crafts Hydroxyalkylation/Oxidative Aromatization to Access Naphthalene Derivatives from Toluenes and Enones
Liu, Haiwang,Ma, Lishuang,Zhou, Rong,Chen, Xuebo,Fang, Weihai,Wu, Jie
, p. 6224 - 6229 (2018/06/11)
Value-added chemicals, γ-aryl ketones and naphthalenes, were conveniently synthesized from readily available toluenes and enones through the synergistic combination of photoredox and Lewis acid catalysis. The direct synthesis of γ-aryl ketones represents a rare example of Giese reactions between benzylic C(sp3)-H and enones that avoids the use of prefunctionalized metallic nucleophiles. Naphthalene derivatives were accessed through a one-pot Giese reaction/Friedel-Crafts hydroxyalkylation/oxidative aromatization sequential transformation.
Methylation of Arenols through Ni-catalyzed C—O Activation with Methyl Magnesium Bromide
Shi, Wen-Juan,Shi, Zhang-Jie
supporting information, p. 183 - 186 (2018/01/15)
Direct alkylation of arenols with alkyl organometallic reagents has never been approached. Herein we reported the first successful example of nickel-catalyzed methylation of arenols with methyl Grignard reagents to construct C(sp2)-C(sp3/
Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C?O or C?N Bond Cleavage
Yang, Ze-Kun,Wang, Dong-Yu,Minami, Hiroki,Ogawa, Hiroyuki,Ozaki, Takashi,Saito, Tatsuo,Miyamoto, Kazunori,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 15693 - 15699 (2016/10/25)
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.
Nickel-Catalyzed Borylation of Aryl and Benzyl 2-Pyridyl Ethers: A Method for Converting a Robust ortho-Directing Group
Tobisu, Mamoru,Zhao, Jiangning,Kinuta, Hirotaka,Furukawa, Takayuki,Igarashi, Takuya,Chatani, Naoto
, p. 2417 - 2421 (2016/08/16)
The nickel-catalyzed borylation of aryl 2-pyridyl ethers via the loss of a 2-pyridyloxy group is described. This method allows a 2-pyridyloxy group to be used as a convertible directing group in C?H bond functionalization reactions. The nickel catalyst can also borylate arylmethyl 2-pyridyl ethers, in which the stereochemistry at the benzylic position is retained in the case of chiral secondary benzylic substrates. (Figure presented.).
Cyclization reaction for the synthesis of polysubstituted naphthalenes in the presence of Au(I) precatalysts
Jagdale, Arun R.,Park, Jong Hyub,Youn, So Won
experimental part, p. 7204 - 7215 (2011/10/17)
Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the π-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.
Mutual activation: Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond of naphtholate
Yu, Da-Gang,Shi, Zhang-Jie
supporting information; experimental part, p. 7097 - 7100 (2011/09/30)
Working together: A new approach of mutual activation between naphtholates and aryl boronic acid derivatives by the formation of borates to facilitate the Suzuki-Miyaura coupling through direct cleavage of the sp2 C-O bond by nickel catalysis is described (see scheme; R′: annulated ring system). Various naphtholates and aryl boronic acid derivatives could be directly coupled in good yields. Copyright
Methylation of arenes via Ni-catalyzed aryl C-O/F activation
Guan, Bing-Tao,Xiang, Shi-Kai,Wu, Tao,Sun, Zuo-Peng,Wang, Bi-Qin,Zhao, Ke-Qing,Shi, Zhang-Jie
, p. 1437 - 1439 (2008/12/21)
Aryl C-O and C-F can be transformed into C-Me via Ni-catalyzed coupling with MeMgBr under mild conditions. The Royal Society of Chemistry.
