Catalyst-free aminobromination of alkenes with N-methyl-p-toluenesulfonamide as nitrogen resource

Zhang, Guangqian; An, Guanghui; Zheng, Jun; Pan, Yi; Li, Guigen

doi:10.1016/j.tetlet.2009.12.059

Cited by 20 publications

(8 citation statements)

References 41 publications

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“…The reaction can give vicinal haloamines in good yields and excellent regioselectivities and stereoselectivities under convenient and mild conditions. 1360 Raghavan et al disclosed a method for the bromosulfonamidation of olefins using a combination of (S,S)-dimethyl-N-(p-tolylsulfonyl)sulfilimine and N-bromosuccinimide as the bromide source. 1362 They studied the synthesis of 3,4unsaturated disubstituted (E)-and (Z)-2-hydroxysulfilimines and their haloamidation reaction.…”

Section: Cohalogenation Reaction With Nbsmentioning

confidence: 99%

“…Under catalyst-free conditions, NBS can be suitably utilized with N -methyl- p -toluenesulfonamide and 4-(trifluoromethyl)benzenesulfonamide to achieve aminobromination. , Zhang and co-workers developed a catalyst-free electrophilic aminobromination system with N -methyl- p -toluenesulfonamide ( p -TsNHCH 3 ) and NBS as the nitrogen and bromine resources, respectively (Scheme ). The reaction can give vicinal haloamines in good yields and excellent regioselectivities and stereoselectivities under convenient and mild conditions …”

Section: Cohalogenation Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Cohalogenation Reaction With Nbsmentioning

confidence: 99%

Section: Cohalogenation Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…Vicinal haloamino moieties are considered as versatile building blocks in organic synthesis because of their synthetic potential for further manipulation by replacement of halogen with diverse nucleophiles. They are synthetic intermediates for functional materials and biologically active compounds. , In the past several decades, a number of procedures have been developed for vicinal aminobromination using various combinations of reagents and catalysts, which includes important examples such as N , N -dihalo sulphonamides, N , N -dihalo carbamates, N -halo carbamates, , N -bromoacetamide, N , N -dibromo phosphoramidate, S , S -dimethyl- N -( p -toluenesulfonyl)-sulfilimine/NBS, TsNBr 2 /TsNH 2, N -methyl- p -toluenesulfonamide/NBS and cyanamide/NBS, KI-NBS-TsNH 2 and others. − Very recently, Yeung and his co-workers reported a catalyst and metal free protocol for the bromoamidation of unactivated olefins using 4-(trifluoromethyl)benzenesulfonamide and N -bromosuccinimide as nitrogen and bromine source . In contrast, we have developed a much simpler protocol for the synthesis of aminobromine using a single reagent (Table , entry 6).…”

Section: Resultsmentioning

confidence: 99%

A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂

et al. 2016

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N,N-Dibromo-p-toluene sulfonamide (TsNBr2) has been found to be an effective reagent for various aminofunctionalization reactions. This reagent behaves both as an electrophilic bromine source as well as amine to react with olefins under different conditions to yield aminoether, imidazoline, diamine and amino bromine. The reaction proceeds rapidly under mild conditions with high regioselectivity. Olefins react with TsNBr2 in moist THF to form δ-amino ether at room temperature. Treatment of TsNBr2 with olefin in MeCN at room temperature produced imidazoline in high yield. Further modification of the reaction condition resulted in the development of a one-step procedure for the synthesis of N-acetyl,N'-tosyl diamine derivatives directly from olefin. When the olefin was treated with 2.4 mol equiv of TsNBr2 in the presence of K2CO3, N,N'-ditosyl diamine derivative was obtained in moderate yield. Instantaneous formation of aminobromine was observed when an olefin was treated with the reagent in dry CH2Cl2 at room temperature.

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“…Sulfonamides are usually used as the most suitable nitrogen sources for aminohalogenation of α,β-unsaturated olefins, including TsNCl 2 [13][14][15], TsNH 2 /NBS [31][32][33][34][35] and NsNCl 2 [2,[40][41][42]. In our continuing study on this reaction, we tried to employ benzamides as nitrogen sources to replace sulfonamides.…”

Section: Introductionmentioning

confidence: 99%

The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

et al. 2010

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The combination of benzamide and NCS was found to be an efficient nitrogen/halogen source for aminohalogenation of β-nitrostyrenes. The reaction was convenient to carry out by using 4-dimethylaminopyridine as the catalyst, resulting in vicinal dichlorinated haloamino nitroalkanes with opposite regiochemistry to that generated from other electron-deficient olefins observed previously. The reaction proceeded smoothly at room temperature with good yields and excellent regioselectivities. A mechanism involving a chloronium intermediate was proposed to explain the resulting regiochemistry. The current system explored a new type of nitrogen sources for aminohalogenation of functionalized olefins.

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Catalyst-free aminobromination of alkenes with N-methyl-p-toluenesulfonamide as nitrogen resource

Cited by 20 publications

References 41 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂

The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

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Catalyst-free aminobromination of alkenes with N-methyl-p-toluenesulfonamide as nitrogen resource

Cited by 20 publications

References 41 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr2

The combination of benzamides/NCS as nitrogen/halogen sources for aminohalogenation of β-nitrostyrenes resulting in dichlorinated haloamides

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A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂