Synthesis of γ-Lactams via Pd(II)-Catalyzed C(sp3)-H Olefination Using a Self-Cleaving Polyfluoroethylsulfinyl Directing Group

Nan-Qi Shao; Yu-Hao Chen; Chen Li; Dong-Hui Wang

doi:10.1021/acs.orglett.0c00326

Synthesis of γ-Lactams via Pd(II)-Catalyzed C(sp³)-H Olefination Using a Self-Cleaving Polyfluoroethylsulfinyl Directing Group

Org Lett. 2020 Sep 18;22(18):7141-7146. doi: 10.1021/acs.orglett.0c00326. Epub 2020 Sep 2.

Authors

Nan-Qi Shao¹, Yu-Hao Chen², Chen Li², Dong-Hui Wang¹

Affiliations

¹ Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Rd., Shanghai 200032, China.
² School of Biotechnology & Health Sciences, Wuyi University, 22 Dongcheng Vill., Jiangmen, Guangdong 529020, China.

PMID: 32875802
DOI: 10.1021/acs.orglett.0c00326

Abstract

A monodentate directing group, 2-chlorotetrafluoroethylsulfinylmide (-NHSOCF₂CF₂Cl), for inert C(sp³)-H bond activation is reported. This directing group shows efficient ability in Pd(II)-catalyzed C(sp³)-H olefination. The desired olefination products undergo subsequent Michael addition and in situ expulsion of the auxiliary to provide the free NH γ-lactam products. Preliminary mechanistic studies reveal that the auxiliary group is crucial for C(sp³)-H activation.

Publication types

Research Support, Non-U.S. Gov't