Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3900-3906.DOI: 10.6023/cjoc202304011 Previous Articles     Next Articles

无金属条件下芳基酮与二甲亚砜的α-C(sp3)—H亚甲基化反应合成γ-酮亚砜

肖朵朵, 张建涛, 周鹏*(), 刘卫兵*()   

  1. 广东石油化工学院化学学院 广东茂名 525000
  • 收稿日期:2023-04-08 修回日期:2023-06-25 发布日期:2023-07-12
  • 基金资助:
    国家自然科学基金(21602035); 广东省科学技术厅(2016A020221038); 广东教育厅(2020ZDZX2054); 广东省自然科学基金(2016A030307030); 广东省自然科学基金(2017A030307006)

Metal-Free α-C(sp3)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide

Duoduo Xiao, Jiantao Zhang, Peng Zhou(), Weibing Liu()   

  1. College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
  • Received:2023-04-08 Revised:2023-06-25 Published:2023-07-12
  • Contact: E-mail: lwb409@gdupt.edu.cn; zhoupeng@gdupt.edu.cn
  • Supported by:
    National Natural Science Foundation of China(21602035); Foundation of Department of Science and Technology of Guangdong Province(2016A020221038); Department of Education of Guangdong Province(2020ZDZX2054); Natural Science Foundation of Guangdong Province(2016A030307030); Natural Science Foundation of Guangdong Province(2017A030307006)

A direct α-C(sp3)—H methylenation of aryl ketones to form γ-keto sulfoxides via C(sp3)—H functionalization with dimethyl sulfoxide has been developed. This method is applicable to a wide range of aryl ketones. Moreover, dimethyl sulfoxide (DMSO) in this reaction is used not only as solvent but also as a sulfur-containing unit. The practical value of this transformation highlights the efficient and robust one-pot synthesis of γ-keto sulfoxides. Based on the preliminary experiments, a plausible reaction mechanism is proposed.

Key words: aryl ketone, C(sp3)—H methylenation, metal-free, γ-keto sulfoxides, regioselectivity