Hydroarylation of 2-Aryloxybut-1-en-3-ynes via Pd/Acid-Catalyzed C-H Bond Activation: A Concise Synthesis of 2,3-Bismethylene-2,3-dihydrobenzofurans.

An intramolecular exo-hydroarylation of 2-aryloxy-1,4-disilylbut-1-en-3-ynes via ortho-C-H bond activation under palladium(0) and acid catalysis was found to give 2,3-bis(silylmethylidene)-2,3-dihydrobenzofurans. The two silyl groups present probably promoted the reaction and played a key role in stabilizing the diene moiety in the product. The products readily led to functionalized condensed cycles by a Diels-Alder reaction.