Ruthenium-Catalyzed Chemoselective N-H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides

Xiaofeng Liu; Ying Shao; Jiangtao Sun

doi:10.1021/acs.orglett.0c04229

Ruthenium-Catalyzed Chemoselective N-H Bond Insertion Reactions of 2-Pyridones/7-Azaindoles with Sulfoxonium Ylides

Org Lett. 2021 Feb 5;23(3):1038-1043. doi: 10.1021/acs.orglett.0c04229. Epub 2021 Jan 21.

Authors

Xiaofeng Liu¹, Ying Shao¹, Jiangtao Sun¹

Affiliation

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.

PMID: 33475367
DOI: 10.1021/acs.orglett.0c04229

Abstract

A ruthenium-catalyzed highly chemoselective N-alkylation of 2-pyridones has been developed, affording N-alkylated 2-pyridone derivatives in good yields and excellent N-selectivity. The key to achieve this unprecedented N-H rather than O-H insertion reaction is the use of CpRu(PPh₃)₂Cl as the catalyst and sulfoxonium ylides as the alkylation reagents. Moreover, this protocol is also amenable to 7-azaindoles by slightly varying the reaction conditions. Furthermore, sulfonium ylides are also suitable alkylation reagents, providing the N-alkylated 2-pyridones in good selectivity.