Rh(III)‐Catalyzed C‐H Cyclization of 2‐Arylbenzimidazoles with CF3‐Imidoyl Sulfoxonium Ylides and Further Sc(III)‐Catalyzed Deaminative Hydroxylation

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-16 DOI:10.1002/adsc.202401220

Juting Liao, Ruirui Zhai, Xiaoyang Gao, Hongliang Wu, Dulin Kong, Shuojin Wang, Xun Chen

引用次数: 0

Abstract

An efficient Rh(III)‐catalyzed C‐H bond activation/cyclization of 2‐arylbenzimidazoles with CF3‐imidoyl sulfoxonium ylides has been achieved, yielding diverse CF3‐ and amino‐disubstituted 5,6‐dihydrobenzoimidazo[2,1‐a]isoquinolines, which could undergo a deaminative hydroxylation to access CF3‐ and hydroxy‐disubstituted 5,6‐dihydrobenzoimidazo[2,1‐a]isoquinolines under Sc(OTf)3 catalyst. This developed strategy features easily available starting materials, broad substrate scope, ready scalability and high efficiency. Moreover, the antitumor activities of selected products against some human cancer cell lines were also investigated, and the results indicated that several products show the effective antiproliferative activities.

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Rh(III)-Catalyzed C-H Cyclization of 2-Arylbenzimidazoles with CF3-Imidoyl Sulfoxonium Ylides and Further Sc(III)-Catalyzed Deaminative Hydroxylation

在 Rh(III)催化下，2-芳基苯并咪唑与 CF3-酰亚胺基磺酰亚胺进行了高效的 C-H 键活化/环化反应，得到了多种 CF3-和氨基二取代的 5、6-二氢苯并咪唑并[2,1-a]异喹啉、6-二氢苯并咪唑并[2,1-a]异喹啉，在 Sc(OTf)3 催化剂作用下，这些异喹啉可进行脱氨基羟基化反应，从而得到 CF3-和羟基-二取代的 5,6-二氢苯并咪唑并[2,1-a]异喹啉。所开发的这一策略具有起始材料易得、底物范围广、可随时扩展和效率高等特点。此外，还研究了所选产物对一些人类癌细胞株的抗肿瘤活性，结果表明几种产物具有有效的抗增殖活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.