CuCl/AgSbF6 and Rh-2(OAc)(4) Comparison for the Synthesis of N-O Tethered Three and Five Membered Rings via Diazo Chemistry


MEREY G., Kubilay H. N., Anaç O.

CHEMISTRY LETTERS, vol.50, no.4, pp.668-671, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 4
  • Publication Date: 2021
  • Doi Number: 10.1246/cl.200863
  • Journal Name: CHEMISTRY LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Chemical Abstracts Core, Metadex
  • Page Numbers: pp.668-671
  • Istanbul Technical University Affiliated: Yes

Abstract

Diazocarbonyl compounds are versatile precursors of carbenes leading to various structures by using several metal catalysts, especially copper and rhodium salts. In this study, eight different diazocarbonyls having N-O moiety were used. The N-O tethered structures were prefened because they may allow some useful transformations of the final products into valuable compounds via N-O cleavage. In the presence of a double bond on the -OR function of the starting diazo compound, CuCl/AgSbF6 catalyst yielded only cyclopropyl fused oxazinane/oxazepane derivatives over cyclopropanation while Rh-2(OAc)(4) catalyst was giving mainly isooxazolidinones via C-H insertion.