51527-49-2Relevant academic research and scientific papers
Tf2NH-Catalyzed Amide Synthesis from Vinyl Azides and Alcohols
Zhang, Feng-Lian,Zhu, Xu,Chiba, Shunsuke
supporting information, p. 3138 - 3141 (2015/06/30)
Triflimide (Tf2NH) specifically catalyzed reactions of alcohols and vinyl azides, enabling efficient construction of amides with C-C bond formation through nucleophilic attack of vinyl azides onto the putative carbocation intermediates derived from alcohols are described.
Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
Zakusilo, Dmitry N.,Ryabukhin, Dmitry S.,Boyarskaya, Irina A.,Yuzikhin, Oleg S.,Vasilyev, Aleksander V.
, p. 102 - 108 (2015/02/02)
Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
