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Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids |
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| Authors: | Sien Liu Bangyue He Hongyi Li Xiaofeng Zhang Yaping Shang Prof Weiping Su |
| Institution: | 1. State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Yangqiao West Road 155, Fuzhou, Fujian, 350002 China
University of Chinese Academy of Sciences, Beijing, 100049 P. R. China;2. State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Yangqiao West Road 155, Fuzhou, Fujian, 350002 China |
| Abstract: | The Rh-catalyzed ortho-C(sp2)?H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp2)?H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional groups as well as aliphatic carboxylic acids with diverse structural scaffolds. |
| Keywords: | Acylation Alkylidene Phthalides C?H Bond functionalization Carboxylic acids Directing group |