异喹啉类化合物氮碳转化合成萘衍生物。

IF 12.5 1区 综合性期刊 Q1 MULTIDISCIPLINARY SCIENCES
Tongtong Zhu, Xuhui Cui, Wenjun Ma, Xiujuan Qi, Hao Wei
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引用次数: 0

摘要

杂芳烃骨架编辑在合成化学中越来越受欢迎。转化单个原子产生具有明显不同性质的分子,从而促进有效的分子交换,可广泛用于合成功能分子。在此,我们提出了一种方便的异喹啉类氮碳单原子嬗变方案,该方案受Wittig反应的启发,使取代萘衍生物易于获得。该反应使用一种廉价且市售的酰化磷作为碳源,以提供各种取代萘。这种转化成功的关键是通过开环形成一个三烯中间体,经过6π电环化和消除过程,得到萘产品。此外,该策略使13CH3PPh3I作为商业13C源易于合成13C标记的萘,并有利于修改C─H功能化的导向基团。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines

Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines
Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges that can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations in isoquinolines, which is inspired by the Wittig reaction and enables easy access to substituted naphthalene derivatives. The reaction uses an inexpensive and commercially available phosphonium ylide as the carbon source to furnish a wide range of substituted naphthalenes. The key to the success of this transformation is the formation of a triene intermediate through ring opening, which undergoes 6π-electrocyclization and elimination processes to afford the naphthalene product. Furthermore, this strategy enables the facile synthesis of 13C-labeled naphthalenes using 13CH3PPh3I as a commercial 13C source and facilitates modifying the directing group for C─H functionalization.
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来源期刊
Science Advances
Science Advances 综合性期刊-综合性期刊
CiteScore
21.40
自引率
1.50%
发文量
1937
审稿时长
29 weeks
期刊介绍: Science Advances, an open-access journal by AAAS, publishes impactful research in diverse scientific areas. It aims for fair, fast, and expert peer review, providing freely accessible research to readers. Led by distinguished scientists, the journal supports AAAS's mission by extending Science magazine's capacity to identify and promote significant advances. Evolving digital publishing technologies play a crucial role in advancing AAAS's global mission for science communication and benefitting humankind.
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