Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides

• DOI: 10.1021/acs.orglett.0c04084
• Publication Date: 2021-01-04T17:23:57Z
• Authors: Ayushee; Monika Patel; Priyanka Meena; Kousar Jahan; Prasad V. Bharatam; Akhilesh K. Verma
• Keywords: 01 natural sciences; 0104 chemical sciences

We investigated a base-promoted protocol for the intermolecular anti-Markovnikov hydroamidation of vinyl arenes with arylamides to furnish the arylethylbenzamides with excellent chemo- and regioselectivity. The reaction tolerates an extensive variety of functional groups and has been successfully extended with electronically varied handles, aminobenzamides, electron-rich/electron-deficient heterocyclic amides, and vinyl arenes to afford the hydroamidated products. Excellent chemoselectivity was observed for the amide group over amine. The proposed mechanism and vital role of the solvent was well supported by deuterium labeling studies and control experiments.