Catalytic Electrophilic Halogenation of Arenes with Electron-Withdrawing Substituents

Autor:	Weijin Wang, Xiaoxue Yang, Rongheng Dai, Zixi Yan, Jialiang Wei, Xiaodong Dou, Xu Qiu, Hongliang Zhang, Chen Wang, Yameng Liu, Song Song, Ning Jiao
Rok vydání:	2022
Předmět:	Colloid and Surface Chemistry Halogenation Electrons Hydrogen Bonding General Chemistry Acids Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 144:13415-13425
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.2c06440
Popis:	The electrophilic halogenation of arenes is perhaps the simplest method to prepare aryl halides, which are important structural motifs in agrochemicals, materials, and pharmaceuticals. However, the nucleophilicity of arenes is weakened by the electron-withdrawing substituents, whose electrophilic halogenation reactions usually require harsh conditions and lead to limited substrate scopes and applications. Therefore, the halogenation of arenes containing electron-withdrawing groups (EWGs) and complex bioactive compounds under mild conditions has been a long-standing challenge. Herein, we describe Brønsted acid-catalyzed halogenation of arenes with electron-withdrawing substituents under mild conditions, providing an efficient protocol for aryl halides. The hydrogen bonding of Brønsted acid with the protic solvent 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) enables this transformation and thus solves this long-standing problem.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a8cd96c8d7217448fc3191c8cd777fc7 https://doi.org/10.1021/jacs.2c06440 Zobrazit plný text záznamu