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EDA Complex from BCP‐Thianthrenium Salt: A Catalyst‐free Strategy To Access 1‐Trifluoromethyl‐3‐quinoxaline Derivatives Bicyclo[1.1.1]pentanes
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-05-13 , DOI: 10.1002/ejoc.202400386
Guofu Zhang 1 , Zijin Luo 1 , Guangyao Mei 2 , Haibo Wang 2 , Chengrong Ding 3
Affiliation  

: The construction of bicyclo[1.1.1.]pentanes (BCPs) typically require the cumbersome use of labile [1.1.1.]propellane in solution and involve multicomponent radical reactions, which commonly produce undesired by‐products that hinder the efficient construction of BCPs. In this paper, we present a catalyst‐free strategy by constructing an electron donor‐acceptor (EDA) complex utilizing the naturally electron‐deficient nature of BCP thianthrenium salt, which were irradiated with visible light to obtain trifluoromethyl‐BCP radicals through a SET process, subsequently reacted with various substituted quinoxalines. Moreover, the successful structural modification of drug molecule derivatives confirm the utility of this scheme in the field of drug discovery.

中文翻译:

BCP-铊盐的 EDA 络合物:一种获取 1-三氟甲基-3-喹喔啉衍生物双环[1.1.1]戊烷的无催化剂策略

:双环[1.1.1.]戊烷(BCP)的构建通常需要在溶液中繁琐地使用不稳定的[1.1.1.]丙烷,并且涉及多组分自由基反应,这通常会产生不需要的副产物,从而阻碍了双环[1.1.1.]戊烷(BCP)的有效构建BCP。在本文中,我们提出了一种无催化剂策略,利用BCP铊盐的天然缺电子性质构建电子供体-受体(EDA)络合物,并用可见光照射,通过SET过程获得三氟甲基-BCP自由基,随后与各种取代的喹喔啉反应。此外,药物分子衍生物的成功结构修饰证实了该方案在药物发现领域的实用性。
更新日期:2024-05-13
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