Gold- and Brønsted Acid-Catalysed Deacyloxylative Cycloaromatisation of 1,6-Diyne Esters to 11H-Benzo[a]fluorenes and 13H-Indeno[1,2-l]phenanthrenes

Corentin Antoine Baratay, Wenhai Li, Mitch Mathiew, Lei Yu, Sara Helen Kyne, Weidong Rao, Philip Wai Hong Chan

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Abstract

A synthetic method to prepare 11H-benzo[a]fluorenes and 13H-indeno[1,2-l]phenanthrenes that relies on the gold(I)- and Brønsted acid-mediated deacyloxylative cycloaromatisation of 1,6-diyne esters under reaction conditions that did not require the exclusion of moisture or air is described. The reaction mechanism was delineated to involve an initial gold(I)-catalysed 1,2-acyloxy migration and 5-exo-trig cyclisation pathway. This was followed by 1,5-enyne rearrangement and Brønsted acid-assisted deacyloxylative aromatisation to give the polyaromatic hydrocarbon (PAH) product.

Original languageEnglish
Pages (from-to)1313-1318
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number7
DOIs
Publication statusPublished - 30 Mar 2022

Keywords

  • deacyloxylative cycloaromatisation
  • gold
  • homogeneous catalysis
  • polyaromatic hydrocarbons
  • synthetic methods

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