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Synthesis of 2-arylbenzofuran-3-carbaldehydes via an organocatalytic [3+2] annulation/oxidative aromatization reaction. 2018

Huiwen Zhang, and Chunmei Ma, and Ziwei Zheng, and Rengwei Sun, and Xinhong Yu, and Jianhong Zhao
State Key Laboratory of Bioengineering Reactors and Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China. xhyu@ecust.edu.cn zjhpharm@ecust.edu.cn.

A novel organocatalytic [3+2] annulation/oxidative aromatization reaction of enals with 2-halophenols or β-naphthols is reported. This process enables chemo- and regioselective access to 2-arylbenzofuran-3-carbaldehydes without the use of transition metals or strong oxidants. Preliminary mechanistic studies reveal that an unprecedented, organocatalytic, direct α-arylation pathway is involved.

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