A convenient palladium catalyzed synthesis of symmetric biaryls, biheterocycles and biaryl chiral diamides |
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Authors: | Shyamaprosad Goswami Avijit Kumar Adak Subrata Jana John F. Gallagher |
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Affiliation: | a Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711103, West Bengal, India b School of Chemical Sciences, Dublin City University, Dublin 9, Ireland |
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Abstract: | A series of symmetrical diamido biaryls has been synthesized in good yield by direct homocoupling of iodoarylbenzamides by palladium-catalysis. No cross product has been isolated from the reaction mixture of two different iodoarylbenzamides under similar conditions. However, only in the case of 2-iodo-N-phenylbenzamide, the intramolecularly coupled product phenanthridone has been isolated as a minor product along with the major intermolecularly coupled product. Biphenyl chiral diamides have been synthesized by this coupling method. This coupling reaction also works well with the reductive dimerization of functionalized heterocyclic compounds. Thus 6,6′-dipivaloylamino-3,3′-bipyridine and 6,6′-dimethyl-2,2′-bipyridine have been efficiently synthesized. In two cases, the X-ray crystal structures have been solved to establish the structures of symmetrical and chiral diamido biaryls and their supramolecular networks. |
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Keywords: | Symmetric biaryls Palladium catalyzed reaction Homocoupling Ullmann reaction Biaryl chiral diamides |
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