Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles

Tomoya Miura, Tsuneaki Biyajima, Tetsuji Fujii, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

186 Citations (Scopus)

Abstract

N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

Original languageEnglish
Pages (from-to)194-196
Number of pages3
JournalJournal of the American Chemical Society
Volume134
Issue number1
DOIs
Publication statusPublished - Jan 11 2012
Externally publishedYes

ASJC Scopus subject areas

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

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