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N‐Alkynylindoles were divergently cyclized for the synthesis of multifused N‐heterocycles. An ortho‐aryl palladium species was added to the α position of an ynamine to generate (Z)‐6‐alkylidene/benzylidene‐6H‐isoindolo[2,1‐a]indoles, while Pt‐catalyzed β‐addition through π‐activation gave 5‐alkyl/arylindolo[2,1‐a]isoquinolines. Double cyclizations using PdCl2 and oxidant afforded bright yellow benzo[7,8]indolizino[2,3,4,5‐...
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