Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 35, Pages 4927-4931Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100860
Keywords
Difluoromethyl; Fluorine; Ketones; Radical Brook rearrangement; Trifluoromethyl
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The paper presents a simple one-pot-two-step process for the synthesis of 1-difluoromethyl 1,4-diketones through Mn-catalyzed radical Brook rearrangement. The methodology can also be used for the synthesis of 1-trifluoromethyl 1,4-diketones. The resulting products can be efficiently converted to fluoroalkyl substituted furans, thiophenes, pyrroles, and pyridazines, which are important structural motifs in natural products and pharmaceuticals.
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.
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