- Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex
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Abstract: A novel silica supported ferrocene appended N-heterocyclic carbene-palladium complex (SilFemBenzNHC@Pd) has been prepared and characterized by using fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). This novel complex served as a robust heterogeneous catalyst for the synthesis of biaryls via homocoupling of aryl boronic acids under base-free conditions in water. Recyclability experiments were executed successfully for six successive runs. Graphic Abstract: [Figure not available: see fulltext.]
- Khanapure, Sharanabasappa,Pore, Dattaprasad,Jagadale, Megha,Patil, Vaishali,Rashinkar, Gajanan
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p. 2237 - 2249
(2021/01/11)
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- Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles
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A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C-H silylation generates arylamines from unactivated arenes with site selectivity controlled by steric effects. This combination of steps gives direct access to many compounds that cannot be accessed via alternative C-H functionalization methods, including direct C-H amination or the combination of C-H borylation and amination.
- Morstein, Johannes,Kalkman, Eric D.,Cheng, Chen,Hartwig, John F.
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p. 5244 - 5247
(2016/11/02)
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- Homocoupling reactions of terminal alkynes and arylboronic compounds catalyzed by in situ formed Al(OH)3-supported palladium nanoparticles
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Palladium nanoparticles supported on newly generated Al(OH)3was found to be a highly efficient catalyst in oxidative homo-couplings of (Het)aryl alkynes, (Het)arylboronic acids and potassium (Het)aryltrifluoroborates, respectively. Moderate to excellent yields of symmetrical 1,3-diynes and biaryls were obtained under mild conditions.
- Li, Xing,Li, Dongjun,Bai, Yana,Zhang, Congxia,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
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supporting information
p. 6996 - 7002
(2016/10/14)
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- Homocoupling of arylboronic acids catalyzed by 1,10-phenanthroline-ligated copper complexes in air
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The efficient homocoupling of arylboronic acids was achieved by using the catalytic combination of inexpensive copper salts and 1,10-phenanthroline as aligand. The homocoupling reaction proceeds at ambient temperature in air without any additives such as base or oxidant. This method tolerates various substituents on the arylboronic acids such as halogens, carbonyls, and a nitro group. As a result, 25 symmetrical biaryls were obtained from readily available arylboronic acids in 19-92% isolated yields. A binuclear (μ- hydroxido)copper complex is assumed as the catalytically active species, which undergoes efficient transmetalation with arylboronic acids to produce dinuclear arylcopper complexes. The binuclear structure is assumed to be essential for the bimetallic reductive elimination of biaryls as well as the oxidative restoration of the catalyst. Wiley-VCH Verlag GmbH & Co, KGaA.
- Kirai, Naohiro,Yamamoto, Yoshihiko
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experimental part
p. 1864 - 1867
(2009/08/17)
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- Combined Directed ortho Metalation/Suzuki-Miyaura cross-coupling strategies. Regiospecific synthesis of chlorodihydroxybiphenyls and polychlorinated biphenyls
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(Chemical Equation Presented) The Directed ortho Metalation (DoM)/Suzuki-Miyaura cross-coupling strategy is applied for the regiospecific construction of all isomeric monochloro and selected dichloro and trichloro 2,3-dihydroxybiphenyls (DHBs). The combined methodology highlights iterative DoM processes, hindered Suzuki-Miyaura couplings, and advantages in diversity in approaches from commercial starting materials leading to provision of chloro-DHBs as single isomers in high purity and on a gram scale. The syntheis of several PCBs are also reported.
- Nerdinger,Kendall,Cai,Marchart,Riebel,Johnson,Yin,Henaff,Eltis,Snieckus
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p. 5960 - 5967
(2008/02/09)
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- Homocoupling of arylboronic acids with a catalyst system consisting of a palladium(II) N-heterocyclic carbene complex and p-benzoquinone
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In the presence of 1-3 mol% SIPr-ligated Pd(OAc)2 and 0.6 equivalent of p-benzoquinone, various arylboronic acids underwent homocoupling in MeOH at ambient temperature to produce symmetrical biaryls in 38-96% yields. Georg Thieme Verlag Stuttgart.
- Yamamoto, Yoshihiko
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p. 1913 - 1916
(2008/03/13)
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