General, Mild, and Intermolecular Ullmann-Type Synthesis of Diaryl and Alkyl Aryl Ethers Catalyzed by Diol−Copper(I) Complex

• Published in: Journal of organic chemistry Vol. 74; no. 10; pp. 3675 - 3679
• Main Authors: Naidu, Ajay B, Jaseer, E. A, Sekar, Govindasamy
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 15-05-2009
• Subjects: Acetonitriles - chemistry; Alcohols - chemistry; Anthracenes - chemistry; Catalysis; Catalysts: preparations and properties; Chemistry; Copper - chemistry; Ethers - chemical synthesis; Ethers - chemistry; Exact sciences and technology; General and physical chemistry; Kinetics and mechanisms; Ligands; Organic chemistry; Organometallic Compounds - chemistry; Reactivity and mechanisms; Stereoisomerism; Temperature; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Arylation; Diol; Catalytic reaction; Transition element complexes; Ether; Mild operating conditions; Alcohol; Steric hindrance; Transition metal Complexes; Copper I Complexes; Chemical coupling; Ullmann reaction; Phenols; Aromatic compound; Copper I Iodides; Chemical synthesis; Catalyst; Univalent metal Complexes; Functional group
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo900438e

A wide range of diaryl ethers and alkyl aryl ethers are synthesized through intermolecular C(aryl)−O bond formation from the corresponding aryl iodides/aryl bromides and phenols/alcohols through Ullmann-type coupling reaction in the presence of a catalytic amount of easily available (±)-diol L3-CuI complex under very mild reaction conditions. Less reactive aryl bromides can also be used for O-arylation of phenols under the same reaction conditions without increasing the reaction temperature, catalyst loading, and time. The catalytic system not only is capable of coupling hindered substrate but also tolerates a broad range of a series of functional groups.