Synthesis of 1,2- and 1,3-Dicarboxylic Acids via Pd(II)-Catalyzed Carboxylation of Aryl and Vinyl C−H Bonds

作者: Ramesh Giri , Jin-Quan Yu

DOI: 10.1021/JA8063827

关键词:

摘要: A Pd(II)-catalyzed reaction protocol for the direct carboxylation of benzoic and phenylacetic acid derivatives to form dicarboxylic acids has been developed. The conditions are also applicable vinyl C−H bonds. first insertion Pd−aryl complex from carboxylic characterized by X-ray crystallography.

参考文章(36)
R. Ugo, A. Chiesa, P. Nardi, R. Psaro, Catalysis by palladium salts Journal of Molecular Catalysis. ,vol. 59, pp. 23- 31 ,(1990) , 10.1016/0304-5102(90)85084-U
Y. Mori, J. Tsuji, Organic syntheses by means of metal complexes—VI Tetrahedron. ,vol. 27, pp. 3811- 3819 ,(1971) , 10.1016/S0040-4020(01)98242-0
Rachel H. Munday, Joseph R. Martinelli, Stephen L. Buchwald, Palladium-catalyzed carbonylation of aryl tosylates and mesylates. Journal of the American Chemical Society. ,vol. 130, pp. 2754- 2755 ,(2008) , 10.1021/JA711449E
Carolina Fernández-Rivas, Diego J. Cárdenas, Belén Martín-Matute, Ángeles Monge, Enrique Gutiérrez-Puebla, Antonio M. Echavarren, Synthesis and Structure of New Oxapalladacycles with a Pd−O Bond Organometallics. ,vol. 20, pp. 2998- 3006 ,(2001) , 10.1021/OM0010565
Wing-Yiu Yu, Wing Nga Sit, Kin-Man Lai, Zhongyuan Zhou, Albert S. C. Chan, Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate. Journal of the American Chemical Society. ,vol. 130, pp. 3304- 3306 ,(2008) , 10.1021/JA710555G
Xiaolong Chen, Yuguo Zheng, Yinchu Shen, Natural products with maleic anhydride structure: nonadrides, tautomycin, chaetomellic anhydride, and other compounds. Chemical Reviews. ,vol. 107, pp. 1777- 1830 ,(2007) , 10.1021/CR050029R
Yuzo Fujiwara, Tomio Kawauchi, Hiroshi Taniguchi, Palladium-promoted one-step carboxylation of aromatic compounds with carbon monoxide Journal of The Chemical Society, Chemical Communications. pp. 220- 221 ,(1980) , 10.1039/C39800000220
Alexander D. Ryabov, Cyclopalladated complexes in organic synthesis Synthesis. ,vol. 1985, pp. 233- 252 ,(1985) , 10.1055/S-1985-31169