A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes |
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Authors: | Wai Chung Fu Fuk Yee Kwong |
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Institution: | Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin New Territories Hong Kong, |
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Abstract: | We herein report a denitrogenative palladium-catalyzed cascade for the modular and regioselective synthesis of polysubstituted fluorenes. Hydrazone facilitates the Pd(ii) to Pd(iv) oxidative addition in a Catellani pathway and is also the methylene synthon in the proposed reaction. Aryl iodides and 2-bromoarylaldehyde hydrazones undergo a norbornene-controlled tandem reaction sequence to give a broad scope of fluorenes in the presence of a palladium catalyst. The method described is scalable and adaptable to a three-component reaction with in situ generation of the hydrazone group. Preliminary mechanistic investigations have been conducted.Hydrazone assists Pd(ii)/(iv) oxidative addition and is the methylene synthon in a palladium-catalyzed, norbornene-mediated regioselective synthesis of fluorenes. |
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