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This paper is dedicated to our colleague and dear friend Prof. Victor Snieckus for his exceptional lifetime contribution to organic chemistry.

We disclose herein our detailed investigation into the Barton copper‐promoted C3‐arylation of indoles using triarylbismuth bis(trifluoroacetates). The arylation of unsubstituted 1H‐indole using Barton's conditions gave a low yield of the C3‐arylated indole, along with small amounts of the product of double C2/C3‐arylation and traces of the product of C2 arylation. On the contrary, the arylation of indoles blocked at the C2 position is highly efficient, affording the desired products of C3‐arylation in good to excellent yields. The reaction operates under simple conditions, shows good substrate scope, excellent functional group compatibility, and allows the transfer of electron‐neutral or deficient aryl groups. Computational studies propose a mechanism involving a trifluoroacetate‐assisted C−H activation step.

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