A copper(ii) complex as an intermediate of copper(i)-catalyzed C–N cross coupling of N-phenylaniline with aryl halide by in situ ESI-MS study

2011 ◽  
Vol 47 (23) ◽  
pp. 6686 ◽  
Author(s):  
Chia-Kai Tseng ◽  
Mei-Chun Tseng ◽  
Chien-Chung Han ◽  
Shin-Guang Shyu
Keyword(s):  
Aryl Halide ◽  
Cross Coupling ◽  
Esi Ms

Intermediates of copper(i)-catalyzed C–S cross coupling of thiophenol with aryl halide by in situ ESI-MS study

2011 ◽  
Vol 47 (19) ◽  
pp. 5599 ◽  
Author(s):  
Shao-Wen Cheng ◽  
Mei-Chun Tseng ◽  
Kwang-Hwa Lii ◽  
Chi-Rung Lee ◽  
Shin-Guang Shyu
Keyword(s):  
Aryl Halide ◽  
Cross Coupling ◽  
Esi Ms

scholarly journals Synthesis and Reactivity of (N2P2)Ni Complexes Stabilized by a Novel Diphosphonite Pyridinophane Ligand

2021 ◽  
Author(s):  
Kei Fuchigami ◽  
Michael B. Watson ◽  
Giang N. Tran ◽  
Nigam P. Rath ◽  
Liviu M. Mirica
Keyword(s):  
Photoelectron Spectroscopy ◽  
Aryl Halide ◽  
Bond Formation ◽  
Cross Coupling ◽  
Electrochemical Studies ◽  
Redox Potentials ◽  
Efficient Catalyst ◽  
X Ray ◽  
Ni Species

A series of (N2P2)Ni<sup>II</sup> complexes (N2P2 = P,P’-ditertbutyl-2,11-diphosphonito[3.3](2,6)pyridinophane) stabilized by a modified tetradentate pyridinophane ligand containing two phosphonite groups were synthesized and characterized. Cyclic voltammetry (CV) studies revealed the accessibility of the Ni<sup>I</sup> oxidation state at moderate redox potentials for these Ni<sup>II</sup> complexes. <i>In situ</i> EPR, low-temperature UV-vis, and electrochemical studies were employed to detect the formation of Ni<sup>I</sup> species during the reduction of Ni<sup>II</sup> precursors. Furthermore, the [(N2P2)Ni<sup>I</sup>(CNtBu)](SbF<sub>6</sub>) complex was isolated upon reduction of the Ni<sup>II</sup> precursor with 1 equiv of CoCp<sub>2</sub>, and was characterized by EPR and X-ray photoelectron spectroscopy (XPS). Finally, the (N2P2)Ni<sup>II</sup>Br<sub>2</sub> complex acts as an efficient catalyst for the Kumada cross-coupling of an aryl halide with an aryl or alkyl Grignard, suggesting that the N2P2 ligand can support the various Ni species involved in the catalytic C-C bond formation reactivity.

scholarly journals Synthesis and Reactivity of (N2P2)Ni Complexes Stabilized by a Novel Diphosphonite Pyridinophane Ligand

2021 ◽  
Author(s):  
Kei Fuchigami ◽  
Michael B. Watson ◽  
Giang N. Tran ◽  
Nigam P. Rath ◽  
Liviu M. Mirica
Keyword(s):  
Photoelectron Spectroscopy ◽  
Aryl Halide ◽  
Bond Formation ◽  
Cross Coupling ◽  
Electrochemical Studies ◽  
Redox Potentials ◽  
Efficient Catalyst ◽  
X Ray ◽  
Ni Species

A series of (N2P2)Ni<sup>II</sup> complexes (N2P2 = P,P’-ditertbutyl-2,11-diphosphonito[3.3](2,6)pyridinophane) stabilized by a modified tetradentate pyridinophane ligand containing two phosphonite groups were synthesized and characterized. Cyclic voltammetry (CV) studies revealed the accessibility of the Ni<sup>I</sup> oxidation state at moderate redox potentials for these Ni<sup>II</sup> complexes. <i>In situ</i> EPR, low-temperature UV-vis, and electrochemical studies were employed to detect the formation of Ni<sup>I</sup> species during the reduction of Ni<sup>II</sup> precursors. Furthermore, the [(N2P2)Ni<sup>I</sup>(CNtBu)](SbF<sub>6</sub>) complex was isolated upon reduction of the Ni<sup>II</sup> precursor with 1 equiv of CoCp<sub>2</sub>, and was characterized by EPR and X-ray photoelectron spectroscopy (XPS). Finally, the (N2P2)Ni<sup>II</sup>Br<sub>2</sub> complex acts as an efficient catalyst for the Kumada cross-coupling of an aryl halide with an aryl or alkyl Grignard, suggesting that the N2P2 ligand can support the various Ni species involved in the catalytic C-C bond formation reactivity.

Possible intermediates of Cu(phen)-catalyzed C–O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies

2014 ◽  
Vol 43 (29) ◽  
pp. 11410-11417 ◽  
Author(s):  
Hong-Jie Chen ◽  
I-Jui Hsu ◽  
Mei-Chun Tseng ◽  
Shin-Guang Shyu
Keyword(s):  
Mass Spectrometry ◽  
Electrospray Ionization ◽  
Catalytic Reaction ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ionization Mass ◽  
Aryl Bromide ◽  
Reaction Conditions ◽  
Esi Ms

Cu(phen) complexes were observed in the copper(i)-catalyzed C–O coupling reaction using K2CO3 as the base and phen as the ligand under the catalytic reaction conditions by in situ electrospray ionization mass spectrometry (ESI-MS) and EPR analysis.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

ChemInform Abstract: An Efficient Synthesis of Dihydroxyfluorenones via in situ Pd(0)-Catalyzed Cross-Coupling.

ChemInform ◽  
2010 ◽  
Vol 29 (49) ◽  
pp. no-no
Author(s):  
F. L. CISKE ◽  
W. D. JUN. JONES
Keyword(s):  
Cross Coupling ◽  
Efficient Synthesis

scholarly journals Pd Nanoparticles Stabilized by Hypercrosslinked Polystyrene Catalyze Selective Triple C-C Bond Hydrogenation and Suzuki Cross-Coupling

2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
Linda Zh. Nikoshvili ◽  
Nadezhda A. Nemygina ◽  
Tatiana E. Khudyakova ◽  
Irina Yu. Tiamina ◽  
Alexey V. Bykov ◽  
...  
Keyword(s):  
Phase Transfer ◽  
Aryl Halide ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Pd Nanoparticles ◽  
Hypercrosslinked Polystyrene ◽  
Reductive Activation ◽  
Pd Nanoparticle ◽  
Cross Coupling Reaction ◽  
Precursor Decomposition

This paper describes the synthesis of Pd-containing catalysts based on nonfunctionalized hypercrosslinked polystyrene via impregnation with Pd acetate. Developed Pd nanoparticulate catalyst allowed achieving conversion of aryl halide up to 90% in Suzuki cross-coupling reaction under mild conditions and at the absence of phase-transfer agents. During the selective hydrogenation of triple C-C bond of 2-methyl-3-butyn-2-ol, up to 96% selectivity with respect to corresponding olefinic alcohol was found at 95% conversion. The influences of the procedure of catalyst synthesis like precursor decomposition and reductive activation method on Pd nanoparticle formation are discussed.

Nitrile-functionalized pyrrolidinium ionic liquids as solvents for cross-coupling reactions involving in situ generated nanoparticlecatalyst reservoirs

2010 ◽  
Vol 12 (8) ◽  
pp. 1834-1841 ◽  
Author(s):  
Yugang Cui ◽  
Ilaria Biondi ◽  
Manish Chaubey ◽  
Xue Yang ◽  
Zhaofu Fei ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Self‐Assembled Multilayer‐Stabilized Nickel Nanoparticle Catalyst for Ligand‐Free Cross‐Coupling Reactions: in situ Metal Nanoparticle and Nanospace Simultaneous Organization

2016 ◽  
Vol 358 (15) ◽  
pp. 2449-2459 ◽  
Author(s):  
Naoyuki Hoshiya ◽  
Katsumasa Fujiki ◽  
Takahisa Taniguchi ◽  
Tetsuo Honma ◽  
Yusuke Tamenori ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Metal Nanoparticle ◽  
Coupling Reactions ◽  
Nickel Nanoparticle ◽  
Cross Coupling Reactions ◽  
Ligand Free ◽  
Self Assembled ◽  
Nanoparticle Catalyst
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