Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi; Takahiro Eto; Manabu Aoyagi; Reiji Kurinami; Hayato Sakai; Taku Hasobe; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/c9ob02674f

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Naoto Iibuchi, Takahiro Eto, Manabu Aoyagi, Reiji Kurinami, Hayato Sakai, Taku Hasobe, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt₃ suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

Original language	English
Pages (from-to)	851-855
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	5
DOIs	https://doi.org/10.1039/c9ob02674f
Publication status	Published - 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst",

abstract = "Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.",

author = "Naoto Iibuchi and Takahiro Eto and Manabu Aoyagi and Reiji Kurinami and Hayato Sakai and Taku Hasobe and Daisuke Takahashi and Kazunobu Toshima",

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language = "English",

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T1 - Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

AU - Iibuchi, Naoto

AU - Eto, Takahiro

AU - Aoyagi, Manabu

AU - Kurinami, Reiji

AU - Sakai, Hayato

AU - Hasobe, Taku

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by a grant for Scientific Research (B) (No. JP19H02724) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT). Publisher Copyright: © 2020 The Royal Society of Chemistry.

PY - 2020

Y1 - 2020

N2 - Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

AB - Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, the ground and excited state absorption spectra of bis(2-naphthyl)disulfide with or without NEt3 suggested the Lewis acidity of bis(2-naphthyl)disulfide upon photo-irradiation.

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Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Abstract

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