Intermediates of copper(i)-catalyzed C–S cross coupling of thiophenol with aryl halide by <i>in situ</i>ESI-MS study

Cheng, Shao Wen; Tseng, Mei‐Chun; Lii, Kwang Hwa; Lee, Chi Rung; Shyu, Shin Guang

doi:10.1039/c1cc11067e

Cited by 35 publications

(38 citation statements)

References 38 publications

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“…M a n u s c r i p t 16 Scheme 7. Suggested catalytic cycle for copper-catalyzed cross coupling reaction of thiophenol and aryl halide based on detected species by ESI-MS [56].…”

Section: Methodsmentioning

confidence: 99%

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The application of electrospray ionization mass spectrometry to homogeneous catalysis

Vikse

Ahmadi

McIndoe

2014

Coordination Chemistry Reviews

117

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“…M a n u s c r i p t 16 Scheme 7. Suggested catalytic cycle for copper-catalyzed cross coupling reaction of thiophenol and aryl halide based on detected species by ESI-MS [56].…”

Section: Methodsmentioning

confidence: 99%

“…Analysis of the same mixture by positive ion mode ESI revealed only the potassium adducts of thiophenol. An anionic reaction mechanism was proposed based on these observations (Scheme 7) [56]. M a n u s c r i p t 16 Scheme 7.…”

Section: Methodsmentioning

confidence: 99%

The application of electrospray ionization mass spectrometry to homogeneous catalysis

Vikse

Ahmadi

McIndoe

2014

Coordination Chemistry Reviews

117

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“…The preparation of thioethers has been under consideration and widely studied in recent years using palladium [23], nickel [24], cobalt [25], copper [26] and iron salts [27] as catalysts. Migita et al [28] first reported the coupling of aryl halides with thiols using Pd(PPh 3 ) 4 as a catalyst.…”

Section: Introductionmentioning

confidence: 99%

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

2014

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This paper reports a series of novel metal acetylacetonates covalently anchored onto amine functionalized silica/starch composite, prepared by the Schiff condensation of metal acetylacetonates [Co(acac) 2 , Cu(acac) 2 , Pd(acac) 2 , Ru(acac) 3 , Mn(acac) 3 , Co(acac) 3 ] with organically modified 3-aminopropyl silica/starch composite. Different metal acetylacetonates have been chosen with a view to select the most active heterogeneous catalyst. Among various catalysts, covalently anchored Cu(acac) 2 onto amine functionalized silica/starch composite [ASS-Cu(acac) 2 ] was found to be the most active and recyclable catalyst for the one-pot thioetherification and one-pot three component synthesis of 2H-indazoles via consecutive C-N and N-N bond formations. All the catalysts were characterized by FTIR, TGA and AAS analysis and the most active catalyst, [ASS-Cu(acac) 2 ] was further characterized by SEM and TEM. The catalyst could be recovered by simple filtration and reused with almost consistent activity for four consecutive runs.

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“…Shao-Wen Cheng and co-workers have employed ESI-MS to study a C-S cross coupling reaction between thiols and aryl halides, catalyzed by copper (I) (Scheme 15) (Cheng et al, 2011).…”

Section: Copper Catalyzed Coupling Of Thiols With Aryl Halidesmentioning

confidence: 99%

Copper‐catalyzed reactions: Research in the gas phase

Tsybizova

Roithová

2015

Mass Spectrometry Reviews

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Electrospray ionization mass spectrometry (ESI-MS) is becoming an important tool for mechanistic studies in organic and organometallic chemistry. It allows investigation of reaction mixtures including monitoring of reactants, products, and intermediates, studying properties of the intermediates and their reactivity. Studying the reactive species in the gas phase can be advantageously combined with theoretical calculations. This review is focused on ESI-MS studies of copper-catalyzed reactions. Possible effects of the electrospray process on the transfer of the copper complexes to the gas phase are discussed. The plethora of mass spectrometric approaches is demonstrated on copper mediated C-H activations, cross coupling reactions, rearrangements, organocuprate chemistry, and other examples.

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Intermediates of copper(i)-catalyzed C–S cross coupling of thiophenol with aryl halide by in situESI-MS study

Cited by 35 publications

References 38 publications

The application of electrospray ionization mass spectrometry to homogeneous catalysis

The application of electrospray ionization mass spectrometry to homogeneous catalysis

Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

Copper‐catalyzed reactions: Research in the gas phase

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