Related Experiment Video
Updated: Mar 23, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Regioselective, Transition Metal-Free C-O Coupling Reactions Involving Aryne Intermediates
Yuyang Dong1,2, Michael I Lipschutz1,2, T Don Tilley1,2
1Department of Chemistry, University of California , Berkeley, Berkeley, California 94720, United States.
Abstract:
A new transition-metal-free synthetic method for C-O coupling between various aryl halides and alkoxides is described. This type of transformation is typically accomplished using palladium catalysts containing a specialized phosphine ligand. The reactions reported here can be performed under mild, ambient conditions using certain potassium alkoxides and a range of aryl halides, with iodide and bromide derivatives giving the best results. A likely mechanistic pathway involves the in situ generation of an aryne intermediate, and directing groups on the aryl ring inductively control regioselectivity.
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Regioselective Formation of Enolates
Regioselectivity of Electrophilic Additions-Peroxide Effect
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

