HFIP & Brønsted Acid Promoted Direct Distal C-Alkylation of 2-Oxindoles and Anilines with Donor-Acceptor Cyclopropanes,Advanced Synthesis & Catalysis

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HFIP & Brønsted Acid Promoted Direct Distal C-Alkylation of 2-Oxindoles and Anilines with Donor-Acceptor Cyclopropanes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-05-04 , DOI: 10.1002/adsc.202300165
Prasoon Raj Singh ₁ , Manisha Lamba ₂ , Divyasha Singh ₂ , Avijit Goswami ₂

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Installation of an alkyl chain at a specified position in the aromatic ring via metal-free catalysis is very important. In this regard, we have developed a facile metal-free, extremely selective, user-friendly, environmentally benign and cost-effective Friedel-Crafts (FC) alkylation protocol for 2-oxindoles and anilines with donor-acceptor cyclopropanes. Real-time NMR studies reveal that the transformation is governed by the cooperative catalysis of Brønsted acid (TfOH) and HFIP, which facilitates the nucleophilic attack on donor-acceptor cyclopropanes from 2-oxindoles and anilines.

中文翻译：

HFIP 和 Brønsted 酸促进 2-羟吲哚和苯胺与供体-受体环丙烷的直接远端 C-烷基化

通过无金属催化在芳环的特定位置安装烷基链非常重要。在这方面，我们开发了一种简便的无金属、极具选择性、用户友好、环境友好且具有成本效益的 Friedel-Crafts (FC) 烷基化方案，用于 2-oxindoles 和苯胺与供体-受体环丙烷。实时核磁共振研究表明，这种转化受布朗斯台德酸 (TfOH) 和 HFIP 的协同催化控制，这促进了 2-羟吲哚和苯胺对供体-受体环丙烷的亲核攻击。

更新日期：2023-05-04

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