Aryne generation vs. Truce-Smiles and Fries rearrangements during the Kobayashi fragmentation reaction: a new bi-aryl synthesis

Research output: Contribution to journalArticle

  • Authors:
  • O. K. Rasheed
  • I. R. Hardcastle
  • J. Raftery
  • P. Quayle

Abstract

Treatment of ortho-​(trimethysilyl)​aryl phenylsulfonates with a sol. fluoride source initiates a Truce-​Smiles rearrangement leading to the formation of functionalized bi-​aryls [e.g., I → II (74​%)​]​. This new carbon-​carbon bond-​forming reaction proceeds without recourse to transition metal catalysis, under mild reaction conditions and with good functional group compatibility. Safety: precautions should be taken in handling poly-​nitro aroms. to avoid detonation.

Bibliographical metadata

Original languageEnglish
Pages (from-to)8048-8052
Number of pages4
JournalOrganic & Biomolecular Chemistry
Volume13
DOIs
StatePublished - 2015