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

Ayushee, . ; Patel, Monika ; Meena, Priyanka ; Jahan, Kousar ; Bharatam, Prasad V. ; Verma, Akhilesh K. (2021) Base-Mediated Anti-Markovnikov Hydroamidation of Vinyl Arenes with Arylamides Organic Letters, 23 (2). pp. 565-570. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.0c04084

Related URL: http://dx.doi.org/10.1021/acs.orglett.0c04084

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:116248
Deposited On:12 Apr 2021 08:29
Last Modified:12 Apr 2021 08:29

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