Highly Efficient Iron(II) Chloride/<i>N</i>‐Bromosuccinimide‐Mediated Synthesis of Imides and Acylsulfonamides

Wang, Feng; Liu, Hongxia; Fu, Hua; Jiang, Yuyang; Zhao, Yufen

doi:10.1002/adsc.200800668

Cited by 28 publications

(24 citation statements)

References 41 publications

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“…[15] The products were utilized in divergent and short synthesis of unsymmetrical 1,4-dicarbonyl compounds (Scheme 3). The ketene dithioacetal moieties of products 3 n and 4 h were easily converted into thioesters [16] by acidic hydrolysis and methylation to provide 5 a and 5 b in 55 % and 92 % yields, respectively (paths a and b). Concise and designed synthesis of 1,4-diketones, good precursors of heteroaromatics, were accomplished by stepwise Fukuyama coupling reactions [16b] of the g,g-disulfanyl-b,g-unsaturated thioesters.…”

Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement

Murakami¹,

Imoto²,

Matsubara³

et al. 2013

Chemistry A European J

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The first examples of metal-catalyzed extended Pummerer reactions through the activation of sulfoxides are described. The copper-catalyzed reactions of ketene dithioacetal monoxides with alkynyl sulfides and ynamides provided a wide variety of γ,γ-disulfanyl-β,γ-unsaturated carbonyl compounds with an accompanying oxygen rearrangement. The products can be easily converted into 1,4-dicarbonyl compounds and substituted heteroaromatics. DFT calculations and mechanistic experiments revealed a new interesting stepwise addition/oxygen rearrangement mechanism.

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Section: Resultsmentioning

confidence: 99%

Copper‐Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement

Murakami¹,

Imoto²,

Matsubara³

et al. 2013

Chemistry A European J

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“…N ‐Benzoyl‐4‐fluorobenzamide (3k): 3b White solid; R f = 0.25 (PE/AcOEt, 4:1). 1 H NMR (400 MHz, CDCl 3 ): δ = 9.13 (s, 1 H), 7.93–7.83 (m, 4 H), 7.60 (t, J = 7.4 Hz, 1 H), 7.49 (t, J = 7.7 Hz, 2 H), 7.16 (t, J = 7.6 Hz, 2 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Synthesis of Imides from Aldehydes or Alcohols and Amine Hydrochloride Salts

Zhang

2015

Eur J Org Chem

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“…84d,e We developed an efficient iron(II) chloride/NBS mediated method for the synthesis of imides and N-acyl-substituted sulfonamides by coupling thioesters with carboxamides/sulfonamides. 85 The rhodium-and ruthenium-catalyzed sulfamidation of aldehydes using a carbon-hydrogen bond activation strategy has been reported. 86 Our research group developed the copper-catalyzed amidation of sp 2 -carbon-hydrogen bonds of aldehydes in the presence of NBS.…”

Section: Copper-catalyzed Amidation Of Sp 2 -Carbon-hydrogen Bonds Of Aldehydesmentioning

confidence: 99%

Copper-Catalyzed Coupling Reactions

Rao¹,

Fu²

2011

Synlett

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This account summarizes our recent developments in copper-catalyzed coupling reactions, including copper-catalyzed N-, O-, and P-arylations, the formation of carbon-nitrogen and carboncarbon bonds via carbon-hydrogen bond activation, and the synthesis of N-heterocyclic compounds. 1 Introduction and Background 2 Copper-Catalyzed N-, O-, and P-Arylations 2.1 Copper-Catalyzed Synthesis of Primary Aromatic Amines 2.2 Copper-Catalyzed Synthesis of Phenols in Water 2.3 Copper-Catalyzed N-Arylation of Aliphatic Amines and Amino Acids at Room Temperature 2.4 Copper-Catalyzed N-Arylation of N-Heterocycles and Aliphatic Amines in Water 2.5 A General Ligand for Copper-Catalyzed N-, O-, and P-Arylations 3 Copper-Catalyzed Formation of Carbon-Nitrogen and Carbon-Carbon Bonds via Carbon-Hydrogen Bond Activation 3.1 Copper-Catalyzed Amidation of sp 3 -Carbon-Hydrogen Bonds 3.2 Copper-Catalyzed Amidation of sp 2 -Carbon-Hydrogen Bonds of Aldehydes 3.3 Copper-Catalyzed Synthesis of Propargylamines via Carbon-Hydrogen Bond Activation 3.4 Copper-Catalyzed Aerobic Oxidative Couplings of Aromatic Boronic Acids with Terminal Alkynes 4 Copper-Catalyzed Synthesis of N-Heterocyclic Compounds 4.1 Copper-Catalyzed Cascade Synthesis of Quinazolinones 4.2 Copper-Catalyzed Cascade Synthesis of Isoquinolin-1(2H)ones 4.3 Copper-Catalyzed Cascade Synthesis of 1,2,4-Benzothiadiazine 1,1-Dioxides 4.4 Copper-Catalyzed Cascade Synthesis of Quinazolines 4.5 Copper-Catalyzed Cascade Synthesis of Benzimidazoles 4.6 Copper-Catalyzed Cascade Synthesis of 2,5-Disubstituted Imidazolones 4.7 Copper-Catalyzed Cascade Synthesis of 2-Amino-1Hindole-3-carboxylate Derivatives 4.8 Copper-Catalyzed Cascade Synthesis of Benzimidazo[1,2b]isoquinolin-11-ones 4.9 Copper-Catalyzed Synthesis of Triazoles 'on Water' 5

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Highly Efficient Iron(II) Chloride/N‐Bromosuccinimide‐Mediated Synthesis of Imides and Acylsulfonamides

Cited by 28 publications

References 41 publications

Copper‐Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement

Copper‐Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement

Copper‐Catalyzed Synthesis of Imides from Aldehydes or Alcohols and Amine Hydrochloride Salts

Copper-Catalyzed Coupling Reactions

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