Synthesis of N-H-Free 1,4-Dihydroisoquinoline-3(2 H)-ones via Pd-Catalyzed C-H Olefination Using Polyfluorosulfinyl as the Auxiliary Group

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

doi:10.1021/acs.orglett.0c01979

Synthesis of N-H-Free 1,4-Dihydroisoquinoline-3(2 H)-ones via Pd-Catalyzed C-H Olefination Using Polyfluorosulfinyl as the Auxiliary Group

Org Lett. 2020 Aug 7;22(15):5880-5884. doi: 10.1021/acs.orglett.0c01979. Epub 2020 Jul 29.

Authors

Yu-Hao Chen¹, Nan-Qi Shao², Chen Li¹, Dong-Hui Wang²

Affiliations

¹ School of Biotech. & Health Sciences, Wuyi University, 22 Dongcheng Vill., Jiangmen, Guangdong 529020, China.
² CAS 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 Road, Shanghai 200032, China.

PMID: 32790423
DOI: 10.1021/acs.orglett.0c01979

Abstract

A Pd(II)-catalyzed olefination of aryl C-H bonds with a self-cleaving 2-chlorotretafluoroethylsulfinyl (-SOCF₂CF₂Cl) auxiliary was developed. In the reaction mixture, the olefination products underwent in situ Michael addition and the subsequent expulsion of the auxiliary to provide the N-H-free 1,4-dihydroisoquinoline-3(2H)-one products. Mechanistic studies reveal that the auxiliary group is crucial for C-H activation, and Na₂CO₃ and an alcoholic solvent play key roles in facilitating the cleavage of the polyfluoroalkylsulfinyl auxiliary.

Publication types

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