Indium-Catalyzed C−S Cross-Coupling of Aryl Halides with Thiols

• Published in: Journal of organic chemistry Vol. 74; no. 8; pp. 3189 - 3191
• Main Authors: Reddy, V. Prakash, Swapna, K, Kumar, A. Vijay, Rao, K. Rama
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.04.2009; Amer Chemical Soc
• Subjects: Alkanes - chemistry; Carbon Compounds, Inorganic - chemical synthesis; Carbon Compounds, Inorganic - chemistry; Catalysis; Chemistry; Chemistry, Organic; Cross-Linking Reagents - chemistry; Exact sciences and technology; Hydrocarbons, Halogenated - chemical synthesis; Hydrocarbons, Halogenated - chemistry; Indium - chemistry; Iodobenzenes - chemical synthesis; Iodobenzenes - chemistry; Mesylates - chemistry; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Sulfhydryl Compounds - chemical synthesis; Sulfhydryl Compounds - chemistry; Sulfides - chemical synthesis; Sulfides - chemistry; BORONIC ACIDS; IODIDES; PHOSPHINE OXIDE LIGAND; MECHANISM; TRANSITION-METAL; ARYLATION; BOND FORMATION; DIARYL SULFIDES; THIOETHERS; EFFICIENT; Methyl sulfoxide; Catalytic reaction; Thiol; Potassium hydroxide; Alkane; Haloarene; Cross reaction; Aromatic compound; Indium; Organic sulfide; Halogen Organic compounds
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo802731j

Indium-catalyzed C−S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)3 (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 °C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.