60706-24-3Relevant articles and documents
NHC-Nickel Catalyzed C-N Bond Cleavage of Mono-protected Anilines for C-C Cross-Coupling
Xia, Ji-Bao,Zhang, Zheng-Bing
, p. 9609 - 9613 (2020/12/21)
A Ni-catalyzed aryl C-N bond cleavage of mono-protected anilines, N-arylsulfonamides, has been developed. A new N-heterocyclic carbene derived from benzoimidazole shows high reactivity for the C-N cleavage/C-C cross-coupling reaction. The ortho-directing group is not required to break the C-N bond of sulfonyl-protected anilines, which are not limited to π-extended anilines. The mechanistic studies have revealed that a sulfamidomagnesium salt is the key coupling intermediate.
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
supporting information, 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.
Synthesis, spectral and structural characterization of Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) complexes with 2-mercapto-5-methyl-1,3,4-thiadiazole: A Zn(II) complex acting as a new sensitive and selective fluorescent probe for the detection of Hg2+ in H2O-MeOH medium
Bharati, Pooja,Bharti,Bharty,Kashyap,Singh,Singh
, p. 222 - 231 (2013/10/22)
Five new complexes, [Ni(mthd)2(py)2] (1), [Cu(en)2](mthd)2 (2), [H2en][Hg(mthd) 3]2·2H2O (3), [Cd (mthd) 2(o-phen)2]2·H2O (4) and [Zn(mthd)2(bpy)] (5) (Hmthd = 2-mercapto-5-methyl-1,3,4-thiadiazole), have been synthesized. All the complexes have been fully characterized by various techniques: elemental analyses, IR, electronic and fluorescent spectral data. The ligand is present in the deprotonated thiol form in the complexes [Cu(en)2](mthd)2(2)and [Cd(mthd)2(o-phen) 2]2·H2O(4). In complex 2, the ligand isionically bonded, whereas it is covalently bonded through the sulfur in complex 4. In [Ni(mthd)2(py)2] (1) the ligand is N, S chelating bidentate bonded through the thiol sulfur and the thiadiazole ring nitrogen adjacent to it, forming a four membered chelate ring. The ligand is covalently bonded through the deprotonated thiadiazole ring nitrogen adjacent to the thiol sulfur in [Zn(mthd)2(bpy)] (5). The complex anion in [H2en][Hg(mthd)3]2·2H2O (3) has a triangular planar geometry, with bonding through the deprotonated thiolato sulfur atoms from the three ligands. [Zn(mthd)2(bpy)] (5) is highly fluorescent as compared to the other complexes and has been further used as a metal probe for sensing of Hg2+ in H2O-MeOH solution. Complex 5, upon interaction with Hg2+, shows a hypochromic shift in the absorption spectra whereas the emission spectra exhibited 75% quenching fluorescence behavior. The electrochemical studies also suggest the interaction of Hg(II) with the Zn(II) complex, probably via the free thione sulfur.
Cross-coupling of aryl/alkenyl silyl ethers with grignard reagents through nickel-catalyzed CO bond activation
Zhao, Fei,Yu, Da-Gang,Zhu, Ru-Yi,Xi, Zhenfeng,Shi, Zhang-Jie
, p. 1001 - 1003 (2011/12/05)
CO activation and its application have drawn much attention since oxygen-based electrophiles are easily available, less toxic, and more environmentally benign. This letter presents systematically results on the Ni-catalyzed KumadaTamaoCorriu coupling based on siloxy arenes/alkenes, which provides a new strategy of silyl protection/CC bond formation sequence in organic synthesis.
Nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids
Chen, Hu,Huang, Zhongbin,Hu, Xiaoming,Tang, Guo,Xu, Pengxiang,Zhao, Yufen,Cheng, Chien-Hong
experimental part, p. 2338 - 2344 (2011/05/30)
The Suzuki-Miyaura cross-coupling of aryl phosphates using Ni(PCy 3)2Cl2 as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling using Pd and Ni catalysts.
Transition-metal-catalyzed cross-couplings of aryl tosylates or mesylates with organoindium reagents
Zhang, Liang,Luo, Yong,Wu, Jie
supporting information; experimental part, p. 1845 - 1848 (2010/10/02)
The first example of transition-metal-catalyzed cross-coupling reactions of aryl tosylates or mesylates with organoindium compounds is described. The desired carbon-carbon bond formation proceeds under mild conditions to generate the coupling products in
Control of reactive site in Palladium-Catalyzed grignard Cross-Coupling of arenes containing both bromide and triflate
Kamikawa, Takashi,Hayashi, Tamio
, p. 7087 - 7090 (2007/10/03)
Reaction of 4-bromophenyl triflate (1) with phenylmagnesium bromide in the presence of 5 mol % of PdCl2(dppp) gave 97% yield of 4-bromobiphenyl (2a), which was formed by selective replacement of triflate in 1 by phenyl. On the other hand, bromide in 1 was substituted with the phenyl Grignard reagent selectively by use of PdCl2(meo-mop)2 to give 4-biphenyl triflate (3a) in high yield. The selective substitution was demonstrated to take place at the oxidative addition step to a palladium(0) species in a stoichiometric reaction of 1 with palladium(0) phosphine complexes.
