An Orchestrated Unsymmetrical Annulation Episode of C(sp2)–H Bonds with Alkynes and Quinones: Access to Spiro-isoquinolones

A nontrivial Ru-catalyzed one-pot sequential oxidative coupling of a (hetero)arene/vinylic/chromene system with alkyne and quinone is presented; the methyl phenyl sulfoximine (MPS) directing group is vital. This cyclization forms four (two C–C and two C–N) bonds in a single operation and produces unusual spiro-fused-isoquinolones with a broad scope. The release of phenyl methyl sulfoxide makes the MPS group transformable. A deuterium scrambling study sheds light on the reaction path.