Organic Letters 2007-02-01

Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction.

Daniel J St Cyr, Nicolas Martin, Bruce A Arndtsen

Index: Org. Lett. 9 , 449, (2007)

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Abstract

[reaction: see text] A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.