ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Highly Chemoselective Synthesis of Hindered Amides via Cobalt-Catalyzed Intermolecular Oxidative Hydroamidation

preprint
submitted on 25.11.2020, 06:01 and posted on 25.11.2020, 13:07 by Yun-Nian Yin, Rui-Qi Ding, Dong-Chen Ouyang, Qing Zhang, Rong Zhu
α-Tertiary amides are of great importance for medicinal chemistry. However, they are often challenging to access through conventional methods due to reactivity and chemoselectivity issues. Here we report a single-step approach towards such amides via cobalt-catalyzed intermolecular oxidative hydroamidation of unactivated alkenes, using nitriles of either solvent- or reagent-quantities. This protocol is orthogonal to groups that rapidly react under known carbocation amidation conditions such as tertiary alcohols, electron-rich alkenes, ketals, weak C−H bonds, and carboxylic acids. Straightforward access to a diverse array of hindered amides is demonstrated, including a rapid synthesis of an aminoadamantane-derived pharmaceutical intermediate.

History

Email Address of Submitting Author

rongzhu@pku.edu.cn

Institution

Peking University

Country

Beijing

ORCID For Submitting Author

0000-0001-5035-3531

Declaration of Conflict of Interest

No

Exports

Logo branding

Exports