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Silane- and peroxide-free hydrogen atom transfer hydrogenation using ascorbic acid and cobalt-photoredox dual catalysis

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Title: Silane- and peroxide-free hydrogen atom transfer hydrogenation using ascorbic acid and cobalt-photoredox dual catalysis
Authors: Kamei, Yuji Browse this author
Seino, Yusuke Browse this author
Yamaguchi, Yuto Browse this author
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Maeda, Satoshi Browse this author →KAKEN DB
Kojima, Masahiro Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Issue Date: 11-Feb-2021
Publisher: Nature Publishing Group
Journal Title: Nature communications
Volume: 12
Start Page: 966
Publisher DOI: 10.1038/s41467-020-20872-z
Abstract: Hydrogen atom transfer (HAT) hydrogenation has recently emerged as an indispensable method for the chemoselective reduction of unactivated alkenes. However, the hitherto reported systems basically require stoichiometric amounts of silanes and peroxides, which prevents wider applications, especially with respect to sustainability and safety concerns. Herein, we report a silane- and peroxide-free HAT hydrogenation using a combined cobalt/photoredox catalysis and ascorbic acid (vitamin C) as a sole stoichiometric reactant. A cobalt salophen complex is identified as the optimal cocatalyst for this environmentally benign HAT hydrogenation in aqueous media, which exhibits high functional-group tolerance. In addition to its applicability in the late-stage hydrogenation of amino-acid derivatives and drug molecules, this method offers unique advantage in direct transformation of unprotected sugar derivatives and allows the HAT hydrogenation of unprotected C-glycoside in higher yield compared to previously reported HAT hydrogenation protocols. The proposed mechanism is supported by experimental and theoretical studies.
Type: article
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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