Reaching the formidable C-H corners has been one of the top priorities of organic chemists in the recent past. This prompted us to disclose herein a vicinal annulation of 2-iodo benzoates, indoles, and carbazoles with N-embedded 1,6-enynes through 7-/8-membered palladacycles. The relay does not require the assistance of any directing group, leading to multicyclic scaffolds, which are readily diversified to an array of adducts (with new functional tethers and/or three contiguous stereocenters), in which we showcase a rare benzylic mono-oxygenation.
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