Different Selectivities in the Insertions into C(sp2)−H Bonds: Benzofulvenes by Dual Gold Catalysis Competition Experiments

Alex J. Plajer, Lukas Ahrens, Marcel Wieteck, Danilo M. Lustosa, Rasool Babaahmadi, Brian Yates, Alireza Ariafard, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)−H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C−H positions. A bidirectional synthesis with two competing ortho-aryl C−H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C−H bonds with a benzylic methyl group also showed perfect selectivity.

Original languageEnglish
Pages (from-to)10766-10772
Number of pages7
JournalChemistry - A European Journal
Volume24
Issue number42
DOIs
StatePublished - 25 Jul 2018
Externally publishedYes

Keywords

  • C−H insertion
  • benzofulvenes
  • chemoselectivity
  • dual gold catalysis
  • gold vinylidenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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