Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.
Dmitry Shabashov, Olafs Daugulis
文献索引：J. Am. Chem. Soc. 132(11) , 3965-72, (2010)
全文：HTML全文
摘要
We have developed a method for auxiliary-directed, palladium-catalyzed beta-arylation and alkylation of sp(3) and sp(2) C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp(3) C-H bonds can be achieved. If arylation of secondary sp(3) C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp(3) and sp(2) C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.
相关化合物
相关文献：
2012-02-03
[J. Org. Chem. 77(3) , 1217-32, (2012)]
Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition. Pourali AR, et al.
[Bull. Chem. Soc. Ethiop. 28(2) , 305-308, (2014)]
ipso-Nitration of 4-iodo-o-xylene. Zweig A, et al.
[J. Org. Chem. 42(25) , 4049-4052, (1977)]
Towards a practical and efficient copper-catalyzed trifluoromethylation of aryl halides. Schareina T, et al.
[Top. Catal. 55(7-10) , 426-431, (2012)]
Synthesis of 3-arylpropylamine derivatives from aryl halides using Heck reaction. Baek GH, et al.
[Bull. Korean Chem. Soc. 20 , 232-236, (1999)]