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Synthesis of 1‐Tri(di)fluoromethyl 1,4‐Diketones Enabled by Radical Brook Rearrangement
Author(s) -
Zhu Zhihong,
Chen Xiang,
Liu Shanshan,
Zhang Jianjun,
Shen Xiao
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100860
Subject(s) - chemistry , trifluoromethyl , radical cyclization , rearrangement reaction , organic chemistry , medicinal chemistry , stereochemistry , catalysis , alkyl
Herein, we disclose the first and simple one‐pot‐two‐step process to the synthesis of 1‐difluoromethyl 1,4‐diketones, through Mn‐catalyzed radical Brook rearrangement. The methodology is also amenable to the synthesis of 1‐trifluoromethyl 1,4‐diketones. The products are efficiently converted to fluoroalkyl substituted furans, thiophenes, pyrroles and pyridazines, which are important structural motifs in natural products and pharmaceuticals.