Efficient palladium(II)-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives

• Published in: Tetrahedron Vol. 67; no. 31; pp. 5550 - 5555
• Main Authors: Li, Ziyuan, Wang, Yiyun, Huang, Yue, Tang, Changhua, Xu, Jinyi, Wu, Xiaoming, Yao, Hequan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 05.08.2011; Elsevier
• Subjects: Carbonyls; Chemistry; Chemistry, Organic; C–H bond activation; Derivatives; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Homocoupling; Methodology; Organic chemistry; Oxazole; Palladium(II)-catalyzed; Phenyls; Physical Sciences; Preparations and properties; Rings (mathematics); Science & Technology; Tetrahedrons; Thiazole; Palladium(II)-catalyzed; Homocoupling; Thiazole; C–H bond activation; Oxazole; CROSS-COUPLING REACTIONS; 2-PHENYLTHIAZOLES; ACTIVATION; ORGANOMETALLIC CHEMISTRY; BONDS; C-H bond activation; INHIBITORS; Sulfur nitrogen heterocycle; Catalytic reaction; Carbon-hydrogen bond; Chemical bond; Palladium II; Thiazole derivatives; Palladium complex; Silver Acetate; Ketone; Chemical coupling; Carboxylic acid; Dicarboxylic acid; Oxazole derivatives; Palladium II Acetate; Electron acceptor; Electron donor; Oxygen nitrogen heterocycle
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.05.123

An efficient Pd(OAc) 2-catalyzed homocoupling of thiazole-4-carboxylic or oxazole-4-carboxylic derivatives is described. It represents a facile and practical methodology to prepare bis-5,5′-thiazole (oxazole)-4,4′-dicarboxylic derivatives in good to excellent yields. This protocol tolerates a series of substitutions on the thiazole (oxazole) rings, including alkyl, carbonyl, and electron-withdrawing/donating group substituted phenyl groups. [Display omitted]