Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine

• Published in: Tetrahedron letters Vol. 39; no. 19; pp. 2937 - 2940
• Main Authors: Evans, David A, Katz, Jeffrey L, West, Theodore R
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.05.1998; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; SUBSTITUTION; VANCOMYCIN
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(98)00502-4

Diaryl ethers are readily synthesized in high yield at room temperature through the copper(II)-promoted coupling of arylboronic acids and phenols. The reaction is tolerant of a wide range of substituents on both coupling partners. These reaction conditions permit the racemization-free arylation of phenolic amino acids, methodology that has been applied to an efficient synthesis of thyroxine. Diaryl ethers are readily synthesized in high yield at room temperature through the Cu(II)-promoted coupling of arylboronic acids and phenols (eq 1). The reaction is tolerant of a wide range of substituents on both coupling partners. These reaction conditions permit the racemization-free arylation of phenolic amino acids, methodology that has been applied to an efficient synthesis of thyroxine (eq 2).