一锅法合成磺酰基二苯并环辛二酮三氟甲磺酸铟促进含氧芳基乙酸与β-芳基乙烯基砜的双傅克反应

One-pot synthesis of sulfonyl dibenzosuberdiones In(OTf)-promoted double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones.

作者信息

Chang Meng-Yang, Lin Chun-Yi

机构信息

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.

Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.

出版信息

Org Biomol Chem. 2023 Mar 15;21(11):2405-2416. doi: 10.1039/d3ob00149k.

DOI:10.1039/d3ob00149k

PMID:36857673

Abstract

Under open-vessel atmosphere conditions, a one-pot easy-to-operate method for the construction of diverse sulfonyl dibenzosuberdiones is developed In(OTf)-promoted tandem double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones. A plausible mechanism is proposed and discussed in detail. This protocol allows for highly effective sequential intermolecular Michael addition, intramolecular ring-closure and α-benzylic oxidation the formation of two carbon-carbon single (C-C) bonds and one carbon-oxygen double (CO) bond.

摘要

在开放容器气氛条件下，开发了一种一锅法易于操作的构建多种磺酰基二苯并环辛二酮的方法。通过三氟甲磺酸铟促进含氧芳基乙酸与β-芳基乙烯基砜的串联双傅克反应。提出并详细讨论了一种合理的机理。该方法允许高效的顺序分子间迈克尔加成、分子内环化和α-苄基氧化——形成两个碳-碳单键（C-C）和一个碳-氧双键（C=O）。