Organophotocatalyst Enabled Deoxycyclopropanation of Alcohols.

IF 14.3 1区 材料科学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Yongsheng Zhang, Jincheng Wang, Xiaoyan He, Shilin Peng, Lei Yuan, Gang Huang, Yongjin Guo, Xiuhong Lu
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Abstract

Cyclopropane fragments, which widely exist in marketed drugs and natural products, can confer special pharmacological properties to small-molecule drugs. Therefore, developing methods to construct cyclopropanes is of great significance. Nevertheless, the introduction of cyclopropane primarily relies on already-formed cyclopropyl groups, which significantly restricts the diversity of cyclopropane skeletons. Late-stage direct cyclopropanation is still a challenging task. Herein, a photo-induced intermolecular deoxycyclopropanation reaction that employs alcohols as substrates, and 1 mol.% of 2,3,5,6-tetrakis(carbazol-9-yl)-1,4-dicyanobenzene (4CzTPN) as organophotocatalyst is reported. This method proceeds with high transformation efficiency (up to 98% yield) and exhibits broad functional group tolerance, such as primary, secondary, and tertiary alcohols as well as various activated β-halogenated alkenes. This process is mild, easy to operate, and has low equipment requirements. The power of this technology is demonstrated by the late-stage functionalization of five marketed drugs and five natural products.

有机光催化剂催化的醇类脱氧环丙烷化反应。
环丙烷片段广泛存在于市售药物和天然产物中,可赋予小分子药物特殊的药理特性。因此,开发构建环丙烷的方法意义重大。然而,环丙烷的引入主要依赖于已经形成的环丙基,这大大限制了环丙烷骨架的多样性。后期直接环丙烷化仍然是一项具有挑战性的任务。本文报告了一种光诱导分子间脱氧环丙烷化反应,该反应以醇为底物,以 1 mol.% 的 2,3,5,6-四(咔唑-9-基)-1,4-二氰基苯(4CzTPN)为有机光催化剂。该方法的转化效率高(收率高达 98%),并具有广泛的官能团耐受性,如伯醇、仲醇、叔醇以及各种活化的 β 卤代烯烃。该工艺温和、易于操作、设备要求低。五种已上市药物和五种天然产品的后期功能化证明了这项技术的威力。
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 Science
Advanced Science CHEMISTRY, MULTIDISCIPLINARYNANOSCIENCE &-NANOSCIENCE & NANOTECHNOLOGY
CiteScore
18.90
自引率
2.60%
发文量
1602
审稿时长
1.9 months
期刊介绍: Advanced Science is a prestigious open access journal that focuses on interdisciplinary research in materials science, physics, chemistry, medical and life sciences, and engineering. The journal aims to promote cutting-edge research by employing a rigorous and impartial review process. It is committed to presenting research articles with the highest quality production standards, ensuring maximum accessibility of top scientific findings. With its vibrant and innovative publication platform, Advanced Science seeks to revolutionize the dissemination and organization of scientific knowledge.
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