Regioselective aminobromination of terminal alkenes

Śliwińska, Anna; Zwierzak, A.

doi:10.1016/s0040-4020(03)00907-4

Cited by 26 publications

(7 citation statements)

References 12 publications

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“…BPEI can be used alternatively to NBS as an end capping agent: this compound has been properly synthesized using the modified literature procedure sketched in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

et al. 2009

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Syndiotactic polystyrene samples end capped with bromine atoms in benzylic position have been synthesized by terminating the syndiospecific styrene polymerization catalyzed by Cp*TiBn3/B(C6F5)3/Al-Oct3 (Cp* = η5-C5(CH3)5; Bn = CH2Ph, Oct = (CH2)7CH3) with N-bromosuccinimide (NBS) and 2-bromo-2-phenylethylisocyanate (BPEI). The chemical structure of the different polymer end groups was assessed by mono and bidimensional NMR techniques. The evaluation of the relative concentrations of the end groups permitted to give new insights into the bromination reaction and syndiospecific styrene polymerization mechanism. Aspecific bromination of the methine carbon of the growing polymer chain bound to the titanium catalyst was observed when NBS was used as terminating agent. The formation of Ti(III) hydrido complexes in the activation reaction was proved as well as the role of these species as active catalyst in syndiospecific styrene polymerization.

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“…BPEI can be used alternatively to NBS as an end capping agent: this compound has been properly synthesized using the modified literature procedure sketched in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

et al. 2009

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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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“…Reaction products were identified by GC‐MS analysis and by comparison with reference aziridines synthesized by cyclization of bromoamines 8. Yields and selectivities were determined by GC analysis.…”

Section: Methodsmentioning

confidence: 99%

“…Styrene was used as a model olefin in our reactions. The expected product, 2‐phenylaziridine, was synthesized separately as a reference by cyclization of 2‐bromo‐2‐phenylethylamine 8. Initial noncatalytic experiments were carried out with pre‐oxidized halonium sources (“X + ”), such as N ‐halosuccinimide (NXS) or X 2 (X=Br, I).…”

Section: Aziridination Of Styrene With Ammonia Using Nxs or I2 In Thementioning

confidence: 99%

A Micellar Iodide‐Catalyzed Synthesis of Unprotected Aziridines from Styrenes and Ammonia

et al. 2008

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Regioselective aminobromination of terminal alkenes

Cited by 26 publications

References 12 publications

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂

A Micellar Iodide‐Catalyzed Synthesis of Unprotected Aziridines from Styrenes and Ammonia

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Regioselective aminobromination of terminal alkenes

Cited by 26 publications

References 12 publications

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

Synthesis of Syndiotactic Polystyrene Macromonomers End Capped with Bromine Atoms: a Tool for a New Investigation of Styrene Polymerization Mechanism Catalyzed by Monocyclopentadienyl Titanium Compounds

A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr2

A Micellar Iodide‐Catalyzed Synthesis of Unprotected Aziridines from Styrenes and Ammonia

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A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂