Visible-light-induced radical switching using benzothiazolyl sulfides for geminal carbon–carbon bond formation

We propose a 2-benzothiazolylthio group as a novel auxiliary for radical switching. Using an acridinium-based photocatalyst, carbon radicals are generated from α-C-H bonds in sulfides, which are subsequently coupled with electron-deficient alkenes. This approach enables efficient access to γ,γ-disubstituted α-amino acid derivatives <i>via</i> two sequential photoredox reactions.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc01998b
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Visible-light-induced radical switching using benzothiazolyl sulfides for geminal carbon–carbon bond formation

Naoya Hasegawa, Tetsuya Sengoku, Haruto Hijikata, K. SHIBATA
2 citations
Chemical Communications
Radical Photochemical Reactions
1.87
article

Visible-light-induced radical switching using benzothiazolyl sulfides for geminal carbon–carbon bond formation

Naoya Hasegawa, Tetsuya Sengoku, Haruto Hijikata, K. SHIBATA
article en
2 citations

Abstract

We propose a 2-benzothiazolylthio group as a novel auxiliary for radical switching. Using an acridinium-based photocatalyst, carbon radicals are generated from α-C-H bonds in sulfides, which are subsequently coupled with electron-deficient alkenes. This approach enables efficient access to γ,γ-disubstituted α-amino acid derivatives <i>via</i> two sequential photoredox reactions.

Chemical CommunicationsVol. 61(53)
Shizuoka University (JP)
Shorai Foundation for Science and Technology, Japan Society for the Promotion of Science
Openalex Percentile: Top 15%
Radical Photochemical Reactions
1.87
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