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Decarboxylative radical addition of N-Boc-amino acids to acrylonitrile via photoinduced electron transfer using 1,4-dicyanonaphthalene

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Abstract

Decarboxylative radical addition of N-(t-butoxycarbonyl)amino acids to acrylonitrile was achieved by excitation of 1,4-dicyanonaphthalene. The photochemical decarboxylation was highly dependent on the dicyanoarenes used as electron acceptors and on addition of a base. The photoreaction proceeded smoothly to yield the decarboxylative adduct even in the presence of only a catalytic amount of 1,4-dicyanonaphthalene.

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Acknowledgments

This work was supported by a Sasakawa Scientific Research Grant, Japan.

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Authors and Affiliations

  1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui, 910-8507, Japan

    Yasuharu Yoshimi, Shota Hayashi, Keisuke Nishikawa, Yoshiki Okita, Kousuke Maeda & Toshio Morita

  2. Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, 1-1-1 Noji-Higashi, Kusatsu, 525-8577, Japan

    Tatsuya Itou

Authors
  1. Yasuharu Yoshimi
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  2. Shota Hayashi
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  3. Keisuke Nishikawa
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  4. Yoshiki Okita
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  5. Kousuke Maeda
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  6. Toshio Morita
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  7. Tatsuya Itou
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Corresponding author

Correspondence to Yasuharu Yoshimi.

Additional information

This paper is dedicated to Professor Kazuhiko Mizuno of Osaka Prefecture University on the occasion of his retirement.

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Yoshimi, Y., Hayashi, S., Nishikawa, K. et al. Decarboxylative radical addition of N-Boc-amino acids to acrylonitrile via photoinduced electron transfer using 1,4-dicyanonaphthalene. Res Chem Intermed 39, 397–402 (2013). https://doi.org/10.1007/s11164-012-0657-z

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  • DOI: https://doi.org/10.1007/s11164-012-0657-z

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