Synthesis of 1-Tri(di)fluoromethyl 1,4-Diketones Enabled by Radical Brook Rearrangement

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.

Automated summary

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.