Reversible Aromaticity Transfer in a Bora-Cycle: Boron-Ligand Cooperation

Urs Gellrich, Yael Diskin-Posner, Linda J.W. Shimon, David Milstein

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)


Aromaticity is a central concept in chemistry. Reaction pathways involving reversible ligand dearomatization sequences emerged as a powerful tool for bond activation by metal complexes. Exploring this concept with a metal-free system, we have synthesized a pyridine-coordinated aminoborane which undergoes a temperature-induced formal dearomatization of the pyridine ring. NMR studies and DFT calculations revealed that this formal dearomatization sequence led to an aromaticity switch and the formation of a six-π-electron boron-containing heteroaromatic system. Disrupting this aromatic system by coordination of an amine or a carboxylic acid to the boron center enabled N-H activation and O-H cleavage, leading to an unprecedented reversal aromaticity switch.

Original languageEnglish
Pages (from-to)13307-13313
Number of pages7
JournalJournal of the American Chemical Society
Issue number40
Publication statusPublished - Oct 12 2016

ASJC Scopus subject areas

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

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