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羟基导向的钌催化萘酚与叶立德的 - 选择性C-H酰甲基化和环化反应

Hydroxyl-Directed Ruthenium-Catalyzed -Selective C-H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides.

作者信息

Ma Wenbo, Tan Yuqiang, Wang Yang, Li Zhiyi, Li Zheyu, Gu Linghui, Mei Ruhuai, Cheng An

机构信息

Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, School of Pharmacy, Chengdu University, Chengdu 610106, P. R. China.

Department of Pharmacology, Tohoku University, Sendai 980-8578, Japan.

出版信息

Org Lett. 2021 Aug 20;23(16):6200-6205. doi: 10.1021/acs.orglett.1c01684. Epub 2021 Aug 2.

Abstract

Herein, we report a highly efficient ruthenium-catalyzed -selective C(sp)-H acylmethylation of 1-naphthols with α-carbonyl sulfoxonium ylides by utilizing hydroxyl as a weakly coordinating directing group. This new method imparts good reactivity, excellent chemo- and regioselectivity, and broad functional group tolerance and involves mild reaction conditions. The C-H acylmethylated products can be readily cyclized into fluorescent annulated pyrans by a one-pot process.

摘要

在此,我们报道了一种高效的钌催化的1-萘酚与α-羰基硫鎓叶立德的C(sp)-H酰甲基化反应,该反应利用羟基作为弱配位导向基团,具有良好的反应活性、出色的化学和区域选择性、广泛的官能团耐受性,且反应条件温和。C-H酰甲基化产物可通过一锅法轻松环化生成荧光稠合吡喃。

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