33384-77-9Relevant academic research and scientific papers
Hemilabile behavior of a thioether-functionalized N-heterocyclic carbene ligand
Huynh, Han Vinh,Yeo, Chun Hui,Tan, Geok Kheng
, p. 3833 - 3835 (2006)
The truely hemilabile nature of a novel thioether-functionalized N-heterocyclic carbene ligand is demonstrated in a range of Pd(ii) complexes. The Royal Society of Chemistry 2006.
1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds
Johnson, Jahvon,Li, Sihan,Mo, Zixuan,Neary, Michelle C.,Zeng, Haisu,Zhang, Guoqi,Zheng, Shengping
, p. 2610 - 2615 (2020/03/05)
Reductive catalysis with earth-abundant metals is currently of increasing importance and shows potential in replacing precious metal catalysis. In this work, we revealed catalytic hydroboration and hydrosilylation of ketones and aldehydes achieved by a structurally defined manganese(ii) coordination polymer (CP) as a precatalyst under mild conditions. The manganese-catalysed methodology can be applied to a range of functionalized aldehydes and ketones with turnover numbers (TON) of up to 990. Preliminary results on the regioselective catalytic hydrofunctionalization of styrenes by the Mn-CP catalyst are also presented.
Erratum: Redox-Noninnocent Ligand-Supported Vanadium Catalysts for the Chemoselective Reduction of C=X (X = O, N) Functionalities (Journal of the American Chemical Society (2019) 141:38 (15230-15239) DOI: 10.1021/jacs.9b07062)
Zhang, Guoqi,Wu, Jing,Zheng, Shengping,Neary, Michelle C.,Mao, Jincheng,Flores, Marco,Trovitch, Ryan J.,Dub, Pavel A.
, p. 16507 - 16509 (2020/10/14)
Pages 15232, 15233, and 15236. In the original paper, the doublet wave functions for 21 and 21a/21b were incorrectly (Figure Presented). reported as spin-contaminated in sections 2.3 and 2.8 (Figure 3 and Scheme 9, respectively.) This comes from the incorrectly reported expected eigenvalue of 0.75 for the spin-squared operator ??2? for the antiferromagnetically coupled doublet |↓?L|↑↑?V state (originally given in the Supporting Information). The correct expected eigenvalue for the |↓?L|↑↑?V state should be 1.75. The wave functions for 21 and 21a/21b (eigenvalues 1.79 and 1.77/1.66, respectively) are therefore not spincontaminated. The corrected Figure 3 and Scheme 9 are presented below. A corrected Supporting Information file is also provided. The corrections do not affect any of the conclusions of the Article, but slightly decrease the gap between the quartet and doublet spin surfaces. Scheme 3 has been also corrected to reflect the fact that (CH3)3SiCH2 ? radicals can only react based on spin conservation.
Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
Delcaillau, Tristan,Bismuto, Alessandro,Lian, Zhong,Morandi, Bill
supporting information, p. 2110 - 2114 (2019/12/24)
A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.
Palladium-Catalyzed C-S Bond Formation as a Tool for Latent-Active Glycosylation
Hedberg, Christinne,Jessen, Kamilla S.,Hansson, Rikke F.,Heuckendorff, Mads,Jensen, Henrik H.
, p. 7068 - 7072 (2020/10/02)
A high-yielding palladium-catalyzed C-S cross-coupling is presented for utilization in carbohydrate chemistry as a key transformation for attachment of a second chelating sulfur atom that allows the exploitation of a latent-active glycosylation strategy w
Practical and selective hydroboration of aldehydes and ketones in air catalysed by an iron(ii) coordination polymer
Zhang, Guoqi,Cheng, Jessica,Davis, Kezia,Bonifacio, Mary Grace,Zajaczkowski, Cynthia
, p. 1114 - 1121 (2019/03/12)
The in air catalytic hydroboration of ketones and aldehydes with pinacolborane by an iron(ii) coordination polymer (CP) is carried out under mild and solvent-free conditions. The precatalyst is highly active towards a wide range of substrates including functionalized ketones and aldehydes in the presence of KOtBu as an activator, achieving a high turnover number (TON) of up to 9500. Excellent chemoselectivity to aldehydes over ketones was also revealed, which is in sharp contrast with the results obtained under inert atmosphere using the same catalyst system. This catalyst observed here is not only highly efficient but also recyclable for reuse for at least 5 times without losing its effectiveness.
Cobalt(II) Coordination Polymer as a Precatalyst for Selective Hydroboration of Aldehydes, Ketones, and Imines
Wu, Jing,Zeng, Haisu,Cheng, Jessica,Zheng, Shengping,Golen, James A.,Manke, David R.,Zhang, Guoqi
, p. 9442 - 9448 (2018/07/05)
Highly effective hydroboration precatalyst is developed based on a cobalt(II)-terpyridine coordination polymer (CP). The hydroboration of ketones, aldehydes, and imines with pinacolborane (HBpin) has been achieved using the recyclable CP catalyst in the presence of an air-stable activator. A wide range of substrates containing polar C=O or C=N bonds have been hydroborated selectively in excellent yields under ambient conditions.
Steric hindrance effects in tripodal ligands for extraction and back-extraction of Ag+
Hiruta, Yuki,Watanabe, Takafumi,Nakamura, Etsuko,Iwasawa, Naoko,Sato, Hiroyasu,Hamada, Kensaku,Citterio, Daniel,Suzuki, Koji
, p. 9791 - 9798 (2014/03/21)
A novel series of tripodal ligands with thiophenylether arms connected to an anchoring nitrogen has been investigated. Seven tripodal ligands were synthesized by combining methyl, isopropyl, and tert-butyl residue bearing thiophenylether sites as groups w
Searching for local biocatalysts: Bioreduction of aldehydes using plant roots of the Province of Cordoba (Argentina)
Salvano, Mario S.,Cantero, Juan J.,Vazquez, Ana M.,Formica, Stella M.,Aimar, Mario L.
experimental part, p. 16 - 21 (2012/02/01)
A screening for the capacity of wild plants growing in the Province of Cordoba to bioreduce benzaldehyde was carried out. From this study, thirteen species showed quantitative reduction yields to benzyl alcohol, with Conium maculatum showing the best reduction efficiency. This plant was also tested against different substituted benzaldehydes, and quantitative yields of substituted benzylic alcohols were obtained, except for vanillin, where only 27% of vanillic alcohol was formed (main product: 2-methoxyphenol at a 73% yield). A scaling study of the reaction using C. maculatum and benzaldehyde was carried out, and it was observed that high substrate-catalyst relationships reduced the efficiency of the reaction due to side reactions of oxidation. The bioreduction method presented here permits substituted benzylic alcohols to be obtained using an environmentally friendly methodology, with excellent yields produced on a laboratory scale.
Enhanced stereoselectivity of a Cu(II) complex chiral auxiliary in the synthesis of Fmoc-L-γ-carboxyglutamic acid
Smith, Daniel J.,Yap, Glenn P.A.,Kelley, James A.,Schneider, Joel P.
, p. 1513 - 1520 (2011/06/20)
L-γ-Carboxyglutamic acid (Gla) is an uncommon amino acid that binds avidly to mineral surfaces and metal ions. Herein, we report the synthesis of N-R-Fmoc-L-γ-carboxyglutamic acid γ, γ0-tert-butyl ester (Fmoc-Gla(OtBu)2-OH), a suitably protected analogue for Fmoc-based solid-phase peptide synthesis. The residue was synthesized using a novel chiral Cu(II) complex, whose structurebased design was inspired by the blue copper protein rusticyanin. The five-coordinate complex is formed by Shiff base formation between glycine and the novel ligand (S)-2-(N-(2-methylthio)benzylprolyl) aminobenzophenone in the presence of copper. Michael addition of di-tert-butyl methylenemalonate to the R-carbon of the glycine portion of the complex occurs in a diastereoselective fashion. The resulting (S,S)-complex diastereomer can be easily purified by chromatography. Metal complex decomposition followed by Fmoc protection affords the enantiomerically pure amino acid. With the use of this novel chiral complex, the asymmetric synthesis of Fmoc-Gla(OtBu)2-OH was completed in nine steps from thiosalicylic acid in 14.5% overall yield.
