There are five different isomeric pyrolloindoles. Although some of the symmetrical variations have been synthesized, methods to prepare substrates that can be converted to non-symmetrical pyrroloindoles still remain highly desirable. A palladium-catalyzed double reductive N-heterocyclization of dialkenyldinitrobenzenes has been developed to achieve four (types A-D) out of the five isomeric permutations. The present methodology allows for the synthesis of a wide variety of previously elusive and highly functionalized pyrroloindoles. These compounds are desirable targets due to their presence in a number of natural products. The Kosugi-Migita-Stille cross coupling was used as the key reaction for the synthesis of the heteroannulation precursors. The generally mild reaction conditions allowed for broad functional group compatibility and offered significant improvements over previously reported methodology.

Double palladium-catalyzed reductive N-heterocyclization: Synthesis of pyrroloindoles

254th National Meeting (2017)

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