Pyrrole Synthesis via Allylic sp3 C− H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes

S Rakshit, FW Patureau, F Glorius

Index: Rakshit, Souvik; Patureau, Frederic W.; Glorius, Frank Journal of the American Chemical Society, 2010 , vol. 132, # 28 p. 9585 - 9587

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Citation Number: 328

Abstract

A conceptually novel pyrrole synthesis is reported, efficiently merging enamines and (unactivated) alkynes under oxidative conditions. In an intermolecular Rh catalyzed process, the challenging allylic sp3 C− H activation of the enamine substrates is followed by the cyclization with the alkyne (R3= CO2R). Alternatively, in some cases (R3= CN), the enamine can be utilized for a vinylic sp2 C− H activation. A total of 17 examples with yields above ...