Organophotocatalytic access to C-glycosides: multicomponent coupling reactions using glycosyl bromides

Naoya Sawada; Ziyi Yu; Hiryu Takinami; Daichi Inoue; Titli Ghosh; Norihiko Sasaki; Toshiki Nokami; Tsuyoshi Taniguchi; Manabu Abe; Takashi Koike

doi:10.1039/D4CC02833C

Organophotocatalytic access to C-glycosides: multicomponent coupling reactions using glycosyl bromides†

Naoya Sawada,^a Ziyi Yu,^a Hiryu Takinami,^a Daichi Inoue,^a Titli Ghosh,^a Norihiko Sasaki,^ab Toshiki Nokami,

*^ab Tsuyoshi Taniguchi,

^c Manabu Abe

*^d and Takashi Koike

^e

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* Corresponding authors

^a Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho minami, Tottori city, 680-8552 Tottori, Japan

^b Centre for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, 4-101 Koyamacho minami, Tottori city, 680-8552 Tottori, Japan

^c Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology, 1-1-1 Higashi, Tsukuba city, Ibaraki, Japan

^d Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima city, Hiroshima, Japan

^e Department of Applied Chemistry, Faculty of Fundamental Engineering, Nippon Institute of Technology, E24-315, 4-1 Gakuendai, Miyashiro-Machi, Minamisaitama-Gun, 345-8501 Saitama, Japan

Abstract

Photochemical multi-component coupling reactions initiated by the activation of glycosyl bromides in the presence of 1,4-bis(diphenylamino)benzene (BDB) as an organic photocatalyst were developed. C-glycosides accompanied by olefin (di)functionalization were obtained. This method allows us to access various C-glycosides with alkene, carbonyl, alcohol, ether, and amide functionalities.

Chemical Communications

Organophotocatalytic access to C-glycosides: multicomponent coupling reactions using glycosyl bromides†

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Organophotocatalytic access to C-glycosides: multicomponent coupling reactions using glycosyl bromides

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