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; Megumi Sakai; Takumi Sakamaki; Tamejiro Hiyama

doi:10.1002/asia.201701079

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

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

Authors

Yasunori Minami¹, Megumi Sakai², Takumi Sakamaki², Tamejiro Hiyama¹

Affiliations

¹ Research and Development Initiative, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
² Department of Applied Chemistry, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.

PMID: 28766860
DOI: 10.1002/asia.201701079

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.