Themed collection Halogen bonding in organic synthesis and catalysis

9 items
Review Article

Halogen bond-induced electrophilic aromatic halogenations

This review highlights the recent development of halogen bond-induced activations of N-halosuccinimides and N,N-dihalodimethylhydantoins in electrophilic aromatic halogenations.

Graphical abstract: Halogen bond-induced electrophilic aromatic halogenations
Communication

Halogen bonding effect on electrochemical anion oxidation in ionic liquids

The properties of three imidazolium based ionic liquids have been compared and used as solvents for the electrochemical oxidation of various anions.

Graphical abstract: Halogen bonding effect on electrochemical anion oxidation in ionic liquids
Communication

Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst

A chiral organic base catalyst with halogen bond donor functionality was used to promote the asymmetric double Mannich reaction to afford 1,3-diamines in excellent yields with high enantio- and diastereoselectivities.

Graphical abstract: Enantio- and diastereoselective double Mannich reaction of malononitrile with N-Boc imines using quinine-derived bifunctional organoiodine catalyst
From the themed collection: Synthetic methodology in OBC
Communication

A bench-stable N-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles

ortho-Nitro-substituted N-trifluoroacetyl imino-λ3-iodane is a bench-stable trifluoroacetyl nitrene precursor, in which intra- and intermolecular halogen bonding (XB) plays an important role.

Graphical abstract: A bench-stable N-trifluoroacetyl nitrene equivalent for a simple synthesis of 2-trifluoromethyl oxazoles
Communication

Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors

A Mukaiyama aldol reaction can be catalyzed by bidentate halogen bond donors with very high efficiency. The halogenated catalysts were stable over multiple consecutive runs, which supports the halogen-bond-based mode of catalysis.

Graphical abstract: Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors
Open Access Paper

Are bis(pyridine)iodine(I) complexes applicable for asymmetric halogenation?

The enantioselectivity of the iodine(I) transfer process from chiral bis(pyridine)iodine(I) complexes to alkenes is explored.

Graphical abstract: Are bis(pyridine)iodine(i) complexes applicable for asymmetric halogenation?
Paper

In silico characterization and prediction of thiourea-like neutral bidentate halogen bond catalysts

Through DFT calculations, thiourea-like halogen bond (XB)-based catalysts, with XB donor moieties connected via covalent bonds, have been designed and applied to Diels–Alder reaction and sulfa-Michael addition.

Graphical abstract: In silico characterization and prediction of thiourea-like neutral bidentate halogen bond catalysts
Paper

Biological halogen bonds in protein–ligand complexes: a combined QTAIM and NCIPlot study in four representative cases

In this study, the PDB has been inspected for the analysis of HaBs in biological systems, highlighting their importance in four different protein–ligand systems.

Graphical abstract: Biological halogen bonds in protein–ligand complexes: a combined QTAIM and NCIPlot study in four representative cases
Paper

Intermolecular binding preferences of haloethynyl halogen-bond donors as a function of molecular electrostatic potentials in a family of N-(pyridin-2-yl)amides

The roles played by halogen bonds and hydrogen bonds in the crystal structures of N-(pyridin-2-yl)amides were evaluated and rationalised in the context of calculated molecular electrostatic potentials.

Graphical abstract: Intermolecular binding preferences of haloethynyl halogen-bond donors as a function of molecular electrostatic potentials in a family of N-(pyridin-2-yl)amides
9 items

About this collection

This themed collection, Guest Edited by Professors Kelling Donald, Catharine Esterhuysen, Célia Fonseca Guerra and Martin Breugst, is dedicated halogen bonding in organic synthesis and catalysis.
The scope of the collection includes, but is not limited to:
  • Studies involving halogen bonding applications in organic synthesis and catalysis 
  • Theoretical contributions on halogen bonding relevant to organic systems
  • Halogen bonding in chemical biology and biomolecular chemistry
  • Physical organic chemistry of halogen bonding
  • molecular design of organic and supramolecular materials involving halogen bonding
New articles will be added to the collection upon publication; please return to this page frequently to see the collection grow.

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