Catalytic Prenylation and Reverse‐Prenylation of Indoles with Isoprene: Regioselectivity Manipulation by Metal–Hydride

As a basic industrial feedstock, isoprene is employed as building block to install prenyl and reverse‐prenyl groups on indoles. Regioselectivity can be manipulated by the choice of metal‐hydrides. Reverse‐prenylated indoles are attained with high selectivity using Rh–H. By switching to a Pd–H catalyst, selectivity toward prenylated indoles is achieved. This regiodivergent protocol also features high atom‐economy without stoichiometric by‐product formation.

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