A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr2
2016
Rajbongshi, Kamal Krishna | Saikia, Indranirekha | Chanu, Loukrakpam Dineshwori | Roy, Subhasish | Phukan, Prodeep
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.
Show more [+] Less [-]AGROVOC Keywords
Bibliographic information
This bibliographic record has been provided by National Agricultural Library