Iron-Catalyzed Reductive Cyclization of <i>o</i>‑Nitrostyrenes Using Phenylsilane as the Terminal Reductant

Abstract

Using microscale high-throughput experimentation, an efficient, earth-abundant iron phenanthroline complex was discovered to catalyze the reductive cyclization of <i>ortho</i>-nitrostyrenes into indoles via nitrosoarene reactive intermediates. This method requires only 1 mol % of Fe­(OAc)<sub>2</sub> and 1 mol % of 4,7-(MeO)<sub>2</sub>phen and uses phenylsilane as a convenient terminal reductant. The scope and limitations of the method were illustrated with 21 examples, and an investigation into the kinetics of the reaction revealed first-order behavior in catalyst and silane and zero-order behavior with respect to nitrostyrene

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