Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors

Yangjie Fu; Zhaohui Wang; Qiyu Zhang; Zhiyu Li; Hong Liu; Xiaoling Bi; Jiang Wang

doi:10.1039/c9ra10749e

Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors

RSC Adv. 2020 Feb 11;10(11):6351-6355. doi: 10.1039/c9ra10749e. eCollection 2020 Feb 7.

Authors

Yangjie Fu^{1

2}, Zhaohui Wang^{1

2}, Qiyu Zhang^{1

2}, Zhiyu Li¹, Hong Liu^{1

2}, Xiaoling Bi¹, Jiang Wang²

Affiliations

¹ Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, China Pharmaceutical University 24 Tongjiaxiang Nanjing 210009 China bxl@163.com.
² State Key Laboratory of Drug Research, Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences 555 Zu Chong Zhi Road Shanghai 201203 China jwang@simm.ac.cn.

Abstract

In this study, we describe a method using sulfoxonium ylides as carbene precursors to achieve C6-selective acylmethylation of pyridones catalyzed by a ruthenium(ii) complex. This approach featured mild reaction conditions, moderate to excellent yields, high step economy, and had excellent functional group tolerance with good site selectivity. Besides, gram-scale preparation, synthetic utility, and mechanistic studies were conducted. It offers a direct and efficient way to synthesize pyridone derivatives.