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分子内苯炔-酚盐[4+2]环加成反应

Intramolecular Benzyne-Phenolate [4+2] Cycloadditions.

作者信息

Takikawa Hiroshi, Nishii Arata, Takiguchi Hiromu, Yagishita Hirotoshi, Tanaka Masato, Hirano Keiichi, Uchiyama Masanobu, Ohmori Ken, Suzuki Keisuke

机构信息

Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

Present address: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.

出版信息

Angew Chem Int Ed Engl. 2020 Jul 20;59(30):12440-12444. doi: 10.1002/anie.202003131. Epub 2020 May 8.

Abstract

An intramolecular benzyne-phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen-sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph MgLi or nBuLi for halogen-metal exchange to form various benzobarrelenes.

摘要

报道了一种分子内苯炔 - 酚盐的[4 + 2]环加成反应。具有邻位卤代磺酸盐官能团的苯炔前体,通过各种连接基团与酚(盐)相连,经用苯基溴化镁锂(PhMgLi)或正丁基锂(nBuLi)进行卤素 - 金属交换处理后,能高效地发生分子内[4 + 2]环加成反应,生成各种苯并桶烯。

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