Gold(I)-Catalyzed Benzylic C(sp³)−H Functionalizations: Divergent Synthesis of Indole[a]- and [b]-Fused Polycycles

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  • Gold(I)‐Catalyzed Benzylic C(sp<sup>3</sup>)−H Functionalizations: Divergent Synthesis of Indole[<i>a</i>]‐ and [<i>b</i>]‐Fused Polycycles**

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Phenyl azides substituted by an (alkylphenyl)ethynyl group facilitate benzylic sp³(C−H) functionalization in the presence of a JohnPhosAu catalyst, resulting in indole-fused tetra- and pentacycles via divergent N- or C-cyclization. The chemoselectivity is influenced depending on the counter-anion, the electron density of the α-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation originating from a 1, 5-hydride shift. An isotopic labeling experiment demonstrates the involvement of an indolylgold(I) species resulting from a tautomerization that is much faster than the deauration. The formation of a benzylic sp³(C−H) functionalization leading to an indole-fused seven-membered ring is also demonstrated.

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