Copper-Catalyzed Tertiary Alkylative Cyanation for the Synthesis of Cyanated Peptide Building Blocks

Naoki Miwa, Chihiro Tanaka, Syo Ishida, Goki Hirata, Jizhou Song, Takeru Torigoe, Yoichiro Kuninobu, Takashi Nishikata

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In this paper, we report efficient cyanation of various peptides containing the α-bromocarbonyl moiety using a Cu-catalyzed radical-based methodology employing zinc cyanide as the cyanide source. Mechanistic studies revealed that in situ formed CuCN was a key intermediate during the catalytic cycle. Our method could be useful for the synthesis of modified peptides containing quaternary carbons.

Original languageEnglish
Pages (from-to)1692-1697
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number4
DOIs
Publication statusPublished - Jan 29 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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