Related Experiment Video
Updated: Jul 31, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Ruthenium-Catalyzed Synthesis of Aryl and Alkenyl Halides from Fluorosulfonates
Clotilde Plaçais1, Sherif J Kaldas2, Morgan Donnard1
1Laboratoire d'Innovation Moléculaire et Applications (UMR 7042), Université de Strasbourg, Université de Haute-Alsace, CNRS, 25 rue Becquerel, 67087, Strasbourg, France.
Abstract:
Aryl and alkenyl halides are widely used as key intermediates in organic synthesis, particularly for the formation of organometallic reagents or as radical precursors. They are also found in pharmaceutical and agrochemical ingredients. In this work, the synthesis of aryl and alkenyl halides from the corresponding fluorosulfonates using commercially available ruthenium catalysts is reported. Notably, this is the first conversion of phenols to aryl halides that is efficient with chloride, bromide, and iodide. Fluorosulfonates are readily prepared using sulfuryl fluoride (SO2 F2 ) and less expensive substitutes for triflates. Although aryl fluorosulfonates and their reactions are well known, this is the first report of an efficient coupling of alkenyl fluorosulfonates. To finish, it was demonstrated, by means of representative examples, that the reaction is possible in a one-pot process, starting directly from phenol or aldehyde.
Related Concept Videos
Preparation and Reactions of Sulfides
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Radical Substitution: Allylic Bromination
Electrophilic Addition to Alkynes: Hydrohalogenation

