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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Diborylfluoromethane as C1F1 Synthon for the Synthesis of α-Fluoroketones
Nagarajan Ramkumar1, Sergey Belyakov1, Janis Veliks1
1Latvian Institute of Organic Synthesis, Aizkraukles iela 21, Riga LV-1006, Latvia.
Abstract:
The selective α-monofluorination of ketones is a significant synthetic challenge. In this study, we introduce a base-promoted coupling reaction that utilizes carboxylic acid esters and diborylfluoromethane, which serves as synthetic equivalent of a monofluorinated C1 (C1F1) synthon. This reaction provides an efficient and convergent synthetic strategy for making α-fluoroketones. It generates a boron-enolate equivalent that can be subsequently trapped with water and other electrophiles, including alkyl halides and fluorinating agents.
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