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 journalArticle

14 Citations (Scopus)

Abstract

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
Volume138
Issue number40
DOIs
Publication statusPublished - Oct 12 2016

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Reversible Aromaticity Transfer in a Bora-Cycle: Boron-Ligand Cooperation'. Together they form a unique fingerprint.

  • Cite this