54755-53-2Relevant academic research and scientific papers
Copper-catalyzed alkylation of sulfonamides with alcohols
Shi, Feng,Tse, Man Kin,Cui, Xinjiang,Goerdes, Dirk,Michalik, Dirk,Thurow, Kerstin,Deng, Youquan,Beller, Matthias
, p. 5912 - 5915 (2009)
Water is the only by-product in an efficient and atom-economical Cu(OAc)2-catalyzed coupling of alcohols with sulfonamides (see proposed mechanism; Ts= p-toluenesulfonyl). It was discovered that bissulfonylated amidines formed as intermediates when the transhydrogenative C-N bond-forming reaction is carried out in air act as novel ligands to stabilize the catalyst.
Copper-catalyzed N-alkylation of sulfonamides with benzylic alcohols: Catalysis and mechanistic studies
Cui, Xinjiang,Shi, Feng,Tse, Man Kin,Goerdes, Dirk,Thurow, Kerstin,Beller, Matthias,Deng, Youquan
supporting information; experimental part, p. 2949 - 2958 (2010/03/24)
The N-alkylation of sulfonamides with alcohols is efficiently performed in the presence of easily available copper catalysts via hydrogen borrowing methodology. Applying a copper acetate/potassium carbonate system the reaction of sulfonamides and alcohols gave the corresponding secondary amines in excellent yield. In situ HR-MS analysis indicated that bissulfonylated amines are formed under air atmosphere, which act as self-stabilizing Iigands for the catalytic system. UV-visible measurements suggest the interaction between the copper centre and the bissulfonylated amine. Reactions of benzyl alcohol-d 7 with p-toluenesulfonamide, Nbenzyl-p-toluenesulfonamide or N-benzylidenetoluenesulfonamide revealed that the reaction proceeds via a transfer hydrogenation mechanism and the whole process is micro-reversible. Competitive reactions of benzyl alcohol and benzyl alconol-d7 with ptoluenesulfonamide revealed a kinetic isotope effect (kH/kD) of 3.287 (0.192) for the dehydrogenation of benzyl alcohol and 0.611 (0.033) for the hydrogenation of the N-benzylidene-p-toluenesulfonamide intermediate, which suggests that dehydrogenation of the alcohol is the rate-determining step.
