Cobalt-catalyzed homo-coupling of aryl and alkenyl bromide using atmospheric oxygen as oxidant

Chen, Shanyong; Zhang, Ji; Li, Yinghao; Wen, Jun; Bian, Shaoquan; Yu, Xiao‐Qi

doi:10.1016/j.tetlet.2009.09.092

Cited by 33 publications

(25 citation statements)

References 32 publications

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“…Recently Wangelin et al [53] showed yields of up to 86 % using substituted benzylic Grignard reagents to give pure unsubstitued biaryls with reaction completion times as short as 30 min; yet the experimental procedure requires a purge of synthetic air as oxidant. Some other attempts have been published by Yu et al [54] giving yields up to 81% using bromobenzene, Grignard reagents and atmospheric oxygen as oxidant but the reported completion time of 3 hours is still long from a practical point of view.…”

Section: Introductionmentioning

confidence: 99%

Graphene-oxide-supported CuAl and CoAl layered double hydroxides as enhanced catalysts for carbon-carbon coupling via Ullmann reaction

Ahmed

Menzel

Wang

et al. 2017

Journal of Solid State Chemistry

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Two efficient catalyst based on CuAl and CoAl layered double hydroxides (LDHs) supported on graphene oxide (GO) for the carbon-carbon coupling (Classic Ullmann Homocoupling Reaction) are reported. The pure and hybrid materials were synthesised by direct precipitation of the LDH nanoparticles onto GO, followed by a chemical, structural and physical characterization by electron microscopy, X-ray diffraction (XRD), thermogravimetric analysis (TGA), surface area measurements, X-ray photoelectron spectroscopy (XPS) and temperature programmed reduction (TPR). The GO-supported and unsupported CuAl-LDH and CoAl-LDH hybrids were tested over the Classic Ullman Homocoupling Reaction of iodobenzene. In the current study CuAl-and CoAl-LDHs have shown excellent yields (91% and 98%, respectively) at very short reaction times (25 min). GO provides a light-weight, charge complementary and two-dimensional material that interacts effectively with the 2D LDHs, in turn enhancing the stability of LDH. As a result, the recyclability of the heterogeneous catalyst systems is greatly enhanced. After 5 re-use cycles, the catalytic activity of the LDH/GO hybrid is up to 2 times higher than for the unsupported LDH.

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Section: Introductionmentioning

confidence: 99%

Graphene-oxide-supported CuAl and CoAl layered double hydroxides as enhanced catalysts for carbon-carbon coupling via Ullmann reaction

Ahmed

Menzel

Wang

et al. 2017

Journal of Solid State Chemistry

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“…16 Meanwhile, the use of the transition metal halides also will make this reaction not green. 16 Thus, new businesslike and eco-friendly catalysts for the homocoupling reaction are still required.…”

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confidence: 99%

Ni(II) Coordination Polymers Constructed from the Flexible Tetracarboxylic Acid and Different N-Donor Ligands: Structural Diversity and Catalytic Activity

Liu

Huang

Xue

et al. 2015

Crystal Growth & Design

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To seek the effect condition of the complexes on the manufacture of the biaryl compounds, seven Ni(II) complexes, namely, {[Ni(L) 0.5 (bpa)(H 2 O)]·2H 2 O} n (1), {[Ni 2 (L)(dpp) 2 (H 2 O)]·4H 2 O} n (2), {[Ni(L) 0.5 (pbmb)(H 2 O)]·H 2 O} n (3), {[Ni 2 (L)(bmp) 2 (H 2 O)]·7H 2 O} n (4), {[Ni(L) 0.5 (pbib) 1.5 ]·2H 2 O} n (5), {[Ni 2 (L)(pbib) 1.5 ]·3H 2 O} n (6) and [Ni(L) 0.5 (beb) 2 (H 2 O)] n (7) (bpa = 1,2-bis(4-pyridyl)ethane, dpp = 1,3-di(4-pyridyl)propane, pbmb = 1,1′-(1,3-propane)bis-(2-methylbenzimidazole), bmp = 1,5-bis(2-methylbenzimidazol) pentane, pbib = 1,4-bis(imidazol-1-ylmethyl)benzene, beb = 1,4-bis(2-ethylbenzimidazol-1-ylmethyl) benzene), have been gained through hydro(solvo)thermal reactions of 5,5'-(hexane-1,6-diyl)-bis(oxy)diisophthalic acid ligand (H 4 L) with Ni(II) metal ions under the regulation and control of six N-donor ligands. 3-fold interpenetrating complex 1 belongs to a (4,4)-connected 3D bbf net with a vertex symbol of (6 4 ·8 2 )(6 6 ) topology. 3-fold interpenetrating complex 2 presents a (4,4,4)-connected 3D bbf net with a Schäfli symbol of (6 6 ) 2 (6 4 ·8 2 ) topology. 3 features a (3,4)-connected 3,4L13 topology with a Schäfli symbol of (4·6 2 )(4 2 ·6 2 ·8 2 ) topology. 4 possesses a (4,4,4)-connected mog Moganite 3D network fabric and the vertex symbol is (4·6 4 ·8) 2 (4 2 ·6 2 ·8 2 ). 5 takes on a (4,5)-connected architecture and the point symbol is (4·6 9 )(4 2 ·6 6 ·8 2 ). 6 is a (4,7)-connected framework and the Schäfli symbol is (4 5 ·5)(4 7 ·5 3 ·6 11 ). 7 has a (4,4)-connected 4,4L28 topology and the Point (Schäfli) symbol is (4 2 ·6 4 )(4·6 4 ·8). A systematic structural comparison of 1-7 signifies that their frameworks can be regulated through varied conformations of the flexible H 4 L ligand and divers Ndonor ligands. Between the proximal Ni(II) ions, the variable-temperature (2−300 K) magnetic susceptibilities of 6 display overall weak antiferromagnetic coupling. In the complexes-catalyzed homo-coupling reaction of iodobenzene, 3, 5, 6 and 7 have been verified to be effectual catalysts for the synthesis of the biaryl compounds.

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“…This may be due to the difficulty in handling the commercial phenylmagnesium bromide. 10 Most of the reported Grignard reagent based catalytic system 5,8 requires sophisticated set-up to handle the reagents in moisture free environment compared to the present work. noteworthy that the present reaction system is tolerant of aryl chloride functionality (entry 6).…”

Section: Resultsmentioning

confidence: 94%

“…But the problem encountered with these later methods is their two step synthetic route, where the organometallic compounds should be prepared first and then in a separate reaction converted into biaryl product. Recently reported cobalt catalyzed homocoupling of Grignard reagents in one step by Chen et al 10 did not discuss the catalytic mechanism and the system requires comparatively higher amount of catalyst loading than the present system.…”

Section: Introductionmentioning

confidence: 74%

Nickel catalyzed one pot synthesis of biaryls under air at room temperature

Bhat

2013

RSC Adv.

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Cobalt-catalyzed homo-coupling of aryl and alkenyl bromide using atmospheric oxygen as oxidant

Cited by 33 publications

References 32 publications

Graphene-oxide-supported CuAl and CoAl layered double hydroxides as enhanced catalysts for carbon-carbon coupling via Ullmann reaction

Graphene-oxide-supported CuAl and CoAl layered double hydroxides as enhanced catalysts for carbon-carbon coupling via Ullmann reaction

Ni(II) Coordination Polymers Constructed from the Flexible Tetracarboxylic Acid and Different N-Donor Ligands: Structural Diversity and Catalytic Activity

Nickel catalyzed one pot synthesis of biaryls under air at room temperature

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