Al‐MCM‐41: An Efficient and Recyclable Heterogeneous Catalyst for the Synthesis of <i>β</i>‐Hydroxy Thiocyanates in Water

Sayyahi, Soheil; Menati, Saied; Karamipour, Mehri

doi:10.1155/2013/561649

Cited by 5 publications

(3 citation statements)

References 20 publications

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“…b-Hydroxy thiocyanates have been synthesized by the regioselective ring opening of epoxides with NH 4 SCN, in water, at 40 1C, using mesoporous aluminosilicate (Al-MCM-41) as a catalyst (Scheme 6). 8 Several epoxides carrying various substituents were rapidly converted to the corresponding b-hydroxy thiocyanates in good yields. Compared to an alkyl-substituted substrate, the phenyl epoxide was opened with opposite regioselectivity, leading to the secondary thiocyanate.…”

Section: Synthesis Of Thiocyanatesmentioning

confidence: 99%

Recent advances in the chemistry of organic thiocyanates

et al. 2016

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Organic thiocyanates are important synthetic intermediates to access valuable sulfur-containing compounds. In this review the different methods for their preparation and their synthetic applications will be presented. The literature of the last 15 years will be covered, highlighting selected recent advances in the chemistry of this class of compounds. We hope to offer chemists the tools to have a good grasp of this singular functionality and open the door to further progress in this chemistry.

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Section: Synthesis Of Thiocyanatesmentioning

confidence: 99%

Recent advances in the chemistry of organic thiocyanates

et al. 2016

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“…Thiocyanate anion (SCN – ) is a well-known inorganic species and is widely used in solid-state chemistry. There have been some reports of SCN – anion acting as a reactant on solid surfaces, − such as the synthesis of β-hydroxy thiocyanate on Al-MCM-41 surface (a mesoporous aluminosilicate) using NH 4 SCN, thiocyanation of aromatic compounds in aqueous media by silica sulfuric acid and silica boron sulfonic acids using KSCN, and oxidation of SCN – anion by K 2 FeO 4 …”

Section: Introductionmentioning

confidence: 99%

Understanding the Diverse Coordination Modes of Thiocyanate Anion on Solid Surfaces

et al. 2019

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Thiocyanate anion (SCN–) can coordinate to solid surfaces in various coordination modes, endowing the solid surfaces with different structures and electronic and catalytic properties, but the rules that dictate the coordination preference are poorly understood due to the multiple coordination sites of both SCN– and the solid surfaces as well as the SCN–-lattice mismatch. In this article, extensive density functional theory calculations are performed to study the coordination modes of SCN– on some selected solid surfaces. In particular, the influence of surface stress, coverage, and counter cations is discussed at length. It is found that the time-honored principle of hard soft acid base can only partly account for the preference of sulfur or nitrogen coordination to the solid surfaces due to its failure to treat the Lewis acids and bases located at the borderline and to deal with the multiple coordination sites and the SCN–-lattice mismatch. Specific to solid surfaces, the coordination number and coordination strength can be gradually changed by applying stress. Moreover, the interactions of SCN– with the counter cations and solvent (water) can modify its coordination mode, which generally favors sulfur coordination owing to the stronger interaction between the more electronegative dangling nitrogen and the counter cations or water. The coordination of SCN– could modify the electronic and geometric properties of the solid surface, which would benefit the design of catalysts. For example, the SCN– coordination improved the conductivity of β-Ni(OH)2, which is potentially useful in electrocatalysis. This work sheds light on the coordination mode of SCN– with significant implications on a variety of applications that can exploit the coordination chemistry.

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“…Herein as part of our continued efforts to develop green and new catalysis systems with a reduced environmental impact [13][14][15][16], we decided to investigate the application of organophilic clay as a catalyst for synthesis of various 3,4dihydropyrimidin-2(1H)-ones in water.…”

Section: Introductionmentioning

confidence: 99%