The effect of hydrogen bond on Brønsted acid-catalyzed intramolecular hydroamination of unfunctionalized olefins. Issue 38 (23rd September 2015)

• Record Type: Journal Article
• Authors: Li, Ting-Ting; Liu, Gong-Qing; Wang, Yu-Mei; Cui, Bin; Sun, Hui; Li, Yue-Ming
• Is Part Of: Tetrahedron. Volume 71:Issue 38(2015)
• Page Start: 7003
• Page End: 7009
• Publication Date: 2015-09-23
• Subjects: Hydroamination -- 4-Penten-1-amine -- 5-Hexen-1-amine -- 2-Methylpyrrolidine -- 2-Methylpiperidine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.07.003
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The catalytic activity of benzoic acid could be increased by introducing a hydrogen bond donor group at the ortho -position. Preliminary DFT calculation indicated that the activation of CC double bond was realized by the action of both the carboxyl group and the hydrogen bond donor. The amino group was brought to the activated CC bond by the interaction between the carboxyl oxygen and amino proton. This interaction also increased the nucleophilicity of the amino group. Thus, in the presence of 20 mol % of 2-(trifluoromethanesulfonamido)benzoic acid, intramolecular hydroamination of unfunctionalized olefins gave the corresponding products in up to 95% isolated yields. Graphical abstract: