Palladium(0)-catalyzed amination,Stille coupling,and Suzuki coupling of electron-deficient aryl fluorides |
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Authors: | Kim Young Mi Yu Shu |
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Institution: | Chemical Research and Development, Pfizer Global Research & Development-La Jolla Laboratories, 3565 General Atomics Court, San Diego, California 92121, USA. |
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Abstract: | The amination of 2-fluoronitrobenzene was Pd(0) catalyzed at 65 degrees C in DMF, and the effectiveness of the catalysis was ligand-dependent. Among the five catalyst systems investigated, Pd(PPh3)4 was the most effective catalyst. The control experiments revealed that Pd(OAc)2 or PPh3 was not responsible for the catalysis. 4-Fluoro-3-nitro-benzonitrile and 4-fluoro-3-nitro-benzaldehyde also underwent Stille coupling and Suzuki coupling in the presence of Pd(PPh3)4, and the reactions afforded the coupling products in 28-86% yields. The control experiments showed no sign of reaction in the absence of palladium. These results were in agreement with the oxidative addition/reductive elimination pathway, where the oxidative addition could conceivably proceed via the SNAr mechanism. |
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