A Covalently Supported Pyrimidinylphosphane Palladacycle as a Heterogenized Catalyst for the Suzuki–Miyaura Cross Coupling

Farsadpour, Saeid; Ghoochany, Leila Taghizadeh; Shylesh, Sankaranarayanapillai; Dörr, Gunder; Seifert, Andreas; Thiel, Werner R.

doi:10.1002/cctc.201100309

Cited by 27 publications

(11 citation statements)

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“…The observed chemical shifts of the organic amine groups agree well with those of the corresponding organosilane precursors measured in solution 15. Small peaks were also observed at δ =62 and 20 ppm and attributed to ethoxy carbon atoms formed by partial esterification of surface silanol groups by ethanol 16 . 29 Si MAS NMR further confirmed the presence of organic functional groups grafted on the silica support (Supporting Information).…”

Section: Resultssupporting

confidence: 79%

Mechanochemical Synthesis, Photophysical Properties, and X‐ray Structures of N‐Heteroacenes

et al. 2016

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Abstract:The described mechanochemical methodology is an example of a proof-of-concept in which solution-based tedious, poor yielding, and difficult syntheses of pyrazaacenes are achieved under solvent-free ball-milling conditions; the method is easy, high yielding, time-efficient, and environmentally benign. The synthesized compounds also include pyrazaacenes (N-heteroacenes) that are octacene analogues containing pyrene building blocks. The compounds were sparingly soluble in

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Section: Resultssupporting

confidence: 79%

Mechanochemical Synthesis, Photophysical Properties, and X‐ray Structures of N‐Heteroacenes

et al. 2016

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“…[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] By providing the "open" space inside the solid support, the porous materials enabled the catalyst-reactant interactions with much higher efficiency. Two good examples of these porous materials reported in the literature that have been used in catalysis are zeolite- [15][16][17][18] and mesoporous silica- [20][21][22][23][24][25][26][27][28][29] based porous materials. The porous organic polymers have attracted much attention because they are very easy to prepare on a large scale under mild conditions compared with other types of porous materials reported in the literature, which were usually synthesized with expensive organic surfactants or templates, and calcination at high temperature is usually required to obtain opening channels.…”

Section: Introductionmentioning

confidence: 99%

Copper‐Incorporated Porous Polydivinylbenzene as Efficient and Recyclable Heterogeneous Catalyst in Ullmann Biaryl Ether Coupling

et al. 2013

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The preparation of efficient and stable heterogeneous catalyst is very important for organic transformations. Herein, we report a copper‐incorporated porous, Schiff base‐modified polydivinylbenzene (PDVB‐SB‐Cu) as an excellent heterogeneous catalyst in promoting Ullmann biaryl ether coupling reactions. PDVB‐SB‐Cu was synthesized by incorporating copper species into PDVB‐SB. Combined characterizations by using 13C NMR, IR, XPS, N2 adsorption, and TEM indicated the synthesis of copper–Schiff base species on porous PDVB. Catalytic tests in the Ullmann biaryl ether coupling of iodobenzene and phenol indicated that the PDVB‐SB‐Cu catalyst gave high activity similar to that of the homogeneous Schiff base‐stabilized copper catalyst. This good reactivity was likely due to the polymer‐based porous materials, which provided more effective interactions between substrates and catalytic centers. Importantly, PDVB‐SB‐Cu has extraordinary recyclability. The advantages of high activities and good recyclability made the PDVB‐SB‐Cu catalyst a new class of solid‐support transition metal catalysts for fine chemical preparation.

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“…5 All solvents were degassed according to standard techniques before use. Nickel(II) perchlorate hexahydrate was purchased from Sigma Aldrich and used without further purification.…”

Section: General Remarksmentioning

confidence: 99%

P,C-bond cleavage in the ligand sphere of a nickel(ii) complex

et al. 2015

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Reacting nickel(ii)perchlorate with a bidentate P,N-ligand in methanol leads to P,C-bond cleavage and gives a five-coordinate nickel complex wherein the nickel(ii) site is coordinated by a tridentate P,N,P-ligand and a bidentate N,C-ligand. The carbanion of the latter is the result of the P,C-bond cleaving process. The diamagnetic nickel(ii) complex was characterized by means of elemental analysis, NMR spectroscopy, cyclic voltammetry and X-ray structure analysis.

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A Covalently Supported Pyrimidinylphosphane Palladacycle as a Heterogenized Catalyst for the Suzuki–Miyaura Cross Coupling

Cited by 27 publications

References 50 publications

Mechanochemical Synthesis, Photophysical Properties, and X‐ray Structures of N‐Heteroacenes

Mechanochemical Synthesis, Photophysical Properties, and X‐ray Structures of N‐Heteroacenes

Copper‐Incorporated Porous Polydivinylbenzene as Efficient and Recyclable Heterogeneous Catalyst in Ullmann Biaryl Ether Coupling

P,C-bond cleavage in the ligand sphere of a nickel(ii) complex

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