Photocatalytic E → Z isomerization of gem-bromofluoroalkenes: stereoselective synthesis of β-fluorostyrene derivatives

Hayato Kato; Yoshihito Kayaki; Takashi Koike

doi:10.1039/d4ob01658k

Photocatalytic E → Z isomerization of gem-bromofluoroalkenes: stereoselective synthesis of β-fluorostyrene derivatives

Org Biomol Chem. 2025 Jan 6. doi: 10.1039/d4ob01658k. Online ahead of print.

Authors

Hayato Kato¹, Yoshihito Kayaki², Takashi Koike¹

Affiliations

¹ Department of Applied Chemistry, Faculty of Fundamental Engineering, Nippon Institute of Technology, 4-1 Gakuendai, Miyashiro-machi, Minamisaitama-gun, Saitama 345-8501, Japan. koike.takashi@nit.ac.jp.
² Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Institute of Science Tokyo, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.

PMID: 39757929
DOI: 10.1039/d4ob01658k

Abstract

Stereoselective synthesis of β-fluorostyrene derivatives has been achieved. Selective isomerization of gem-bromofluoroalkenyl benzenes bearing various ortho-substituents is enabled by using Ir photocatalysts with high triplet energy. Subsequent one-pot transition-metal (TM)-catalyzed reactions enable pot-economical synthesis of monofluoroalkenes in a stereoselective manner.