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

8 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

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Boron
Pyridine
Chemical activation
Ligands
Switches
Coordination Complexes
Metal complexes
Carboxylic Acids
Carboxylic acids
Discrete Fourier transforms
Amines
Metals
Nuclear magnetic resonance
Electrons
Temperature
pyridine

ASJC Scopus subject areas

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

Cite this

Reversible Aromaticity Transfer in a Bora-Cycle : Boron-Ligand Cooperation. / Gellrich, Urs; Diskin-Posner, Yael; Shimon, Linda J W; Milstein, David.

In: Journal of the American Chemical Society, Vol. 138, No. 40, 12.10.2016, p. 13307-13313.

Research output: Contribution to journalArticle

Gellrich, Urs ; Diskin-Posner, Yael ; Shimon, Linda J W ; Milstein, David. / Reversible Aromaticity Transfer in a Bora-Cycle : Boron-Ligand Cooperation. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 40. pp. 13307-13313.
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