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. 2017 Sep 19;12(18):2399-2403.
doi: 10.1002/asia.201701079. Epub 2017 Aug 30.

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

Yasunori Minami  1 , Megumi Sakai  2 , Takumi Sakamaki  2 , Tamejiro Hiyama  1
Affiliations

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

Yasunori Minami et al. Chem Asian J. .

Abstract

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.

Keywords: C−H activation; alkynes; cycloaddition; palladium; synthetic methods.

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