Copper‐Catalyzed Direct Synthesis of Iodoenamides from Ketoximes

Liang, Hao; Z, Ren; Wang, Yao‐Yu; Zhang, Guan

doi:10.1002/chem.201301785

Cited by 57 publications

(15 citation statements)

References 97 publications

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“…All reactions were performed with 1 a (0.5 mmol), 2 (0.5 mmol), Cu(OAc) 2 (10 mol %), in toluene (2 mL) at 100 8C under N 2 for 6 h, followed by stirring in CH 2 Cl 2 with silica gel at room temperature overnight. [20] In conclusion, we have developed a novel method for the synthesis of sulfone derivatives through the copper-catalyzed coupling of oxime acetates with sodium sulfinates. Scheme 6.…”

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confidence: 99%

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

et al. 2014

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Sulfone derivatives are important synthetic intermediates. However, the general method for their preparation is through traditional coupling reaction: the alkylation of sodium sulfinates with phenacyl halides. Based on our previous work on sodium sulfinates and oxime acetates, we herein report a novel method for sulfone derivatives by oxidative coupling with sodium sulfinates and oxime acetates using copper as catalyst. The sulfonylvinylamine products could be formed in excellent yields. Upon hydrolysis by silica gel in CH2 Cl2 , β-ketosulfones could also be efficiently constructed. Various sulfonylvinylamines and β-ketosulfones were obtained in good to excellent yields under the optimized reaction conditions. Mechanistic studies indicated that this transformation involved copper-catalyzed N-O bond cleavage, activation of a vinyl sp(2) C-H bond, and C-S bond formation. The oxime acetates act as both a substrate and an oxidant, thus the reaction needs no additional oxidants or additives.

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confidence: 99%

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

et al. 2014

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“…Then, intermediate D can be produced after tautomerization of intermediate B to intermediate C and subsequent activation of the vinyl C–H bond by the Cu (III) species. Finally, reductive elimination of intermediate D affords key intermediate E and regenerates MCM‐41‐Sb,Py‐Cu(I)OAc to complete the catalytic cycle . Intermediate E can be isolated in high yield before hydrolysis to target product 3a .…”

Section: Resultsmentioning

confidence: 99%

Heterogeneous copper‐catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β‐keto sulfones

Xia

Huang

You

et al. 2019

Applied Organom Chemis

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An efficient and practical route to β-keto sulfones has been developed through heterogeneous oxidative coupling of oxime acetates with sodium sulfinates by using an MCM-41-supported Schiff base-pyridine bidentate copper (II) complex [MCM-41-Sb,Py-Cu (OAc) 2 ] as the catalyst and oxime acetates as an internal oxidant, followed by hydrolysis. The reaction generates a variety of β-keto sulfones in good to excellent yields. This new heterogeneous copper (II) catalyst can be easily prepared via a simple procedure from readily available and inexpensive reagents and exhibits the same catalytic activity as Cu (OAc) 2 .MCM-41-Sb,Py-Cu (OAc) 2 is also easy to recover and is recyclable up to eight times with almost consistent activity.

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“…Then, intermediate 6 was obtained after tautomerization and the Cu III species activated the vinyl CH. Finally, the desired product 8 was generated from reductive elimination of intermediate 6 (path b) 20 …”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

et al. 2014

View full text Add to dashboard Cite

Sulfone derivatives are important synthetic intermediates. However, the general method for their preparation is through traditional coupling reaction: the alkylation of sodium sulfinates with phenacyl halides. Based on our previous work on sodium sulfinates and oxime acetates, we herein report a novel method for sulfone derivatives by oxidative coupling with sodium sulfinates and oxime acetates using copper as catalyst. The sulfonylvinylamine products could be formed in excellent yields. Upon hydrolysis by silica gel in CH2Cl2, β‐ketosulfones could also be efficiently constructed. Various sulfonylvinylamines and β‐ketosulfones were obtained in good to excellent yields under the optimized reaction conditions. Mechanistic studies indicated that this transformation involved copper‐catalyzed NO bond cleavage, activation of a vinyl sp2 CH bond, and CS bond formation. The oxime acetates act as both a substrate and an oxidant, thus the reaction needs no additional oxidants or additives.

show abstract

Copper‐Catalyzed Direct Synthesis of Iodoenamides from Ketoximes

Cited by 57 publications

References 97 publications

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

Heterogeneous copper‐catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β‐keto sulfones

Copper‐Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives

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