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

Yuji Kamei, Yusuke Seino, Yuto Yamaguchi, Tatsuhiko Yoshino, Satoshi Maeda, Masahiro Kojima () and Shigeki Matsunaga ()
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Yuji Kamei: Hokkaido University
Yusuke Seino: Hokkaido University
Yuto Yamaguchi: Hokkaido University
Tatsuhiko Yoshino: Hokkaido University
Satoshi Maeda: Hokkaido University
Masahiro Kojima: Hokkaido University
Shigeki Matsunaga: Hokkaido University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-020-20872-z

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