- Palygorskite-anchored Pd complexes catalyze the coupling reactions of pyrimidin-2-yl sulfonates
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In this work, an anchored Pd complex (PGS-APTES-Pd(OAc)2) was prepared via simple and green steps from the natural clay mineral palygorskite and was well characterized by XPS, XRD, IR, SEM, and EDX. This complex was further utilized as a fine catalyst for the C-C/C-N coupling reactions of pyrimidin-2-yl sulfonates. Subsequently, the cyclic utilization test indicated the high stability and sustainability of this PGS-APTES-Pd(OAc)2 catalyst, and no activation was required in the recycling process, providing an applicable and reusable catalyst in organic synthesis.
- Zhan, Huiying,Zhou, Rongrong,Chen, Xudong,Yang, Quanlu,Jiang, Hongyan,Su, Qiong,Wang, Yanbin,Li, Jia,Wu, Lan,Wu, Shang
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- Wool-anchored Pd(OAc)2 complex: A highly active and reusable catalyst for desulfurative coupling reactions
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A biomacromolecule-anchored palladium complex, wool-Pd(OAc)2, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind-Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids. Products were isolated in moderate to excellent yields. When 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable of being reused for at least nine rounds, with durable performance and wide substrate tolerance.
- Yang, Quanlu,Quan, Zhengjun,Du, Baoxin,Wu, Shang,Li, Peidong,Sun, Yanxia,Lei, Ziqiang,Wang, Xicun
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p. 4522 - 4531
(2015/09/01)
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- C-C/C-N cross-coupling reactions of aryl sulfonates catalyzed by an eco-friendly and reusable heterogeneous catalyst: Wool-Pd complex
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A well-defined heterogeneous palladium catalyst, supported on biomacromolecule, natural wool fibre, was found to be an effective catalyst for the C-C/C-N coupling of pyrimidin-2-yl sulfonates with arylboronic acids, terminal alkynes or anilines, giving the desired coupling products in good to high yields. The catalyst was characterized by XPS, IR, SEM and ICP. More importantly, the easy experimental handling catalyst is stable, shows negligible metal leaching, and can be reused for at least 10 successive runs. Undoubtedly, a wide scope of reactant, insensitive to the electron effects and the excellent coupling yields make these catalyst systems potentially useful in organic synthesis.
- Yang, Quan-Lu,Quan, Zheng-Jun,Du, Bao-Xin,Wu, Shang,Zhang, Yin-Pan,Li, Pei-Dong,Wang, Ming-Ming,Lei, Zi-Qiang,Wang, Xi-Cun
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p. 59770 - 59779
(2016/11/18)
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- Recyclable palladium catalyst on grapheme oxide for the C-C/C-N cross-coupling reactions of heteroaromatic sulfonates
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Abstract A well-defined heterogeneous palladium catalyst, graphene oxide grafted with PdCl2, was prepared and found to be an effective catalyst for the C-C, C-N coupling of hetero aryl sulfonates with aryl boronic acids, terminal alkynes, amines, respectively, leading to the desired coupling products in moderate to excellent yields. The catalyst was characterized by XRD, IR, SEM, TEM, XPS and ICP. It is worthy noting that this catalyst offers a number of advantages such as high stability and negligible metal leaching. It also retains good activity for at least five successive runs without any additional activation treatment, showing a better performance than the well-known commercial Pd/C catalysts. This approach would be very useful from a practical viewpoint.
- Yang, Quanlu,Quan, Zhengjun,Wu, Shang,Du, Baoxin,Wang, Mingming,Li, Peidong,Zhang, Yinpan,Wang, Xicun
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supporting information
p. 6124 - 6134
(2015/08/03)
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- RETRACTED ARTICLE: Reusable biomacromolecule-Pd complex catalyzed C-C cross-coupling reactions via C-S cleavage of disulfides
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A well-defined heterogeneous palladium catalyst, natural wool supported Pd(OAc)2-complex was found to be an effective catalyst for the C-S bonds cleavage and C-C bonds formation from 1,2-di(pyrimidin-2-yl)disulfane derivatives with arylboronic acids or terminal alkynes, giving the desired coupling products in moderate to excellent yields. The novel catalyst, which is stable and easy handling in experiment, was characterized by XPS, IR, SEM and ICP analysis. Subsequent analysis of the used catalyst after reaction revealed its negligible metal leaching and at least 10 rounds of recycled catalyzing capacity and wide range of substrate tolerance.
- Yang, Quanlu,Wu, Shang,Quan, Zhengjun,Du, Baoxin,Wang, Mingming,Li, Peidong,Zhang, Yinpan,Lei, Ziqiang,Wang, Xicun
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supporting information
p. 8462 - 8471
(2015/10/12)
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- Chemoselective carbon-carbon cross-coupling via palladium-catalyzed copper-mediated C-S cleavage of disulfides
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An efficient method for carbon-carbon bond formation is described. The process employs the palladium-catalyzed copper-mediated cross-coupling of diheteroaryl disulfides with arylboronic acids or alkynes to deliver C-C coupling products through unreactive C-S bond cleavage. The scope of the coupling reactions, including both the disulfides and arylboronic acids or alkynes, are documented.
- Quan, Zheng-Jun,Lv, Ying,Jing, Fu-Qiang,Jia, Xiao-Dong,Huo, Cong-De,Wang, Xi-Cun
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supporting information
p. 325 - 332
(2014/05/20)
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- Palladium(II) catalyzed Suzuki/Sonogashira cross-coupling reactions of sulfonates: An efficient approach to C2-functionalized pyrimidines and pyridines
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Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized. An efficient means to synthesize expanded pyrimidin-2-yl conjugated systems was developed by using Pd(OAc) 2-catalyzed cross-coupling reaction of pyrimidin/pyridin-2-yl sulfonates with arylboronic acids and terminal alkynes. Compared with 2-chloropyrimidines, pyrimidin-2-yl sulfonates can be easily prepared from inexpensive commercial materials and the reactions are more efficient. Copyright
- Quan, Zheng-Jun,Jing, Fu-Qiang,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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supporting information
p. 7175 - 7183
(2013/11/06)
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- Direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes via Pd/Cu-catalyzed phosphonium coupling
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The first chemoselective direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes has been achieved via C-H/C-OH bond activations with direct C(sp2)-C(sp) bond formation, which is in line with ideal synthesis using readily
- Kang, Fu-An,. Lanter, James C,Cai, Chaozhong,Sui, Zhihua,Murray, William V.
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supporting information; experimental part
p. 1347 - 1349
(2010/07/05)
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