Liu, K (Liu, Kun)^{[ 1 ]} ; Tang, S (Tang, Shan)^{[ 1 ]} ; Huang, PF (Huang, Pengfei)^{[ 1 ]} ; Lei, AW (Lei, Aiwen)^{[ 1,2 ]}

Intermolecular [3 + 2] annulation is one of the most straightforward approaches to construct five membered heterocycles. However, it generally requires the use of functionalized substrates. An ideal reaction approach is to achieve dehydrogenative [3 + 2] annulation under oxidant-free conditions. Here we show an electrooxidative [3 + 2] annulation between phenols and N-acetylindoles under undivided electrolytic conditions. Neither external chemical oxidants nor metal catalysts are required to facilitate the dehydrogenation processes. This reaction protocol provides an environmentally friendly way for the selective synthesis of benzofuroindolines. Various N-acetylindoles bearing different C-3 and C-2 substituents are suitable in this electrochemical transformation, furnishing corresponding benzofuroindolines in up to 99% yield.

KeyWords Plus:CROSS-COUPLING REACTION; N-ACETYL INDOLES; OXIDATIVE ANNULATION; 1,3-DIPOLAR CYCLOADDITIONS; ORGANIC ELECTROSYNTHESIS; H FUNCTIONALIZATION; AROMATIC-COMPOUNDS; INTERNAL ALKYNES; RADICAL CATIONS; DIRECT ACCESS

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.

Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.

地址:

电子邮件地址:aiwenlei@whu.edu.cn

原文PDF链接：

https://www.nature.com/articles/s41467-017-00873-1.pdf