One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate

• Published in: Chemistry : a European journal Vol. 16; no. 8; pp. 2355 - 2359
• Main Authors: Fernández-Rodríguez, Manuel A., Hartwig, John F.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 22.02.2010; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Aromatic compounds; aryl bromides; aryl sulfides; Availability; Catalysis; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; cross-coupling; Hydrocarbons, Brominated - chemistry; Joining; Molecular Structure; palladium; Palladium - chemistry; Physical Sciences; Science & Technology; Sulfhydryl Compounds - chemistry; Sulfides; Sulfides - chemical synthesis; Sulfides - chemistry; Synthesis; thiol surrogate; Thiols; Tolerances; HALIDES; SYSTEM; aryl bromides; BOND FORMATION; SULFUR; EFFICIENT METHOD; REARRANGEMENT; S-ARYLATION; cross-coupling; palladium; TRIISOPROPYLSILANETHIOL; INHIBITORS; aryl sulfides; thiol surrogate; ANTAGONISTS
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200902313

Extraordinarily simple, convenient, and efficient: A general and operationally simple one‐pot synthesis of unsymmetrical diaryl sulfides by coupling two different bromoarenes and triisopropylsilanethiol (TIPS‐SH) is reported. This protocol overcomes the narrow availability of arene thiols and their instability to oxidation. These reactions catalyzed by palladium complexes generated from the alkylbisphosphine CyPF‐tBu occur in good to excellent yields with wide scope and high tolerance of functional groups.