The reaction of thio acids with azides: A new mechanism and new synthetic applications

Ning Shangguan, Sreenivas Katukojvala, Rachel Greenberg, Lawrence Williams

Research output: Contribution to journalArticle

265 Scopus citations

Abstract

A new amide synthesis strategy based on a fundamental mechanistic revision of the reaction of thio acids and organic azides is presented. The data demonstrate that amines are not formed as intermediates in this reaction. Alternative mechanisms proceeding through a thiatriazoline intermediate are suggested. The reaction has been applied to the preparation of simple and architecturally complex amides that are difficult to access using conventional methods. The reaction is chemoselective, effective for unprotected substrates, and compatible with aprotic and protic solvents, including water.

Original languageEnglish (US)
Pages (from-to)7754-7755
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number26
DOIs
StatePublished - Jul 2 2003

All Science Journal Classification (ASJC) codes

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

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