Chemoselective Synthesis of α-Fluoromethyl Amides via the Controlled Addition of LiCH 2 F to N-Aryl and N-Alkyl Isocyanates

Davide Castiglione; Alberto Nardi; Margherita Miele; Laura Castoldi; Vittorio Pace

doi:10.1039/d5cc06730h

January 1, 2026Chemical CommunicationsOpen Access

Chemoselective Synthesis of α-Fluoromethyl Amides via the Controlled Addition of LiCH 2 F to N-Aryl and N-Alkyl Isocyanates

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Key Points

The aim is to develop a controlled method for synthesizing α-fluoroacetamides using lithium reagents.
Utilized lithium fluoromethyl reagents for nucleophilic addition
Performed under controlled conditions ensuring chemocontrol
Preserved stereochemical information during synthesis
Successfully synthesized α-fluoroacetamides through the new method
Demonstrated full preservation of stereochemical information
Achieved desired products with high specificity

Implication

Demonstrates the synthesis of α-fluoroacetamides via nucleophilic addition to isocyanates, indicating a chemoselective approach.

Abstract

α-Fluoroacetamides were prepared through the nucleophilic addition of fluoromethyl-lithium to isocyanates. This single synthetic operation takes place under full chemocontrol and complete preservation of the stereochemical information. The protocol is...

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Cite This Study

Castiglione et al. (2026) studied this question.

synapsesocial.com/papers/698828530fc35cd7a8847b92 https://doi.org/10.1039/d5cc06730h

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Chemoselective Synthesis of α-Fluoromethyl Amides via the Controlled Addition of LiCH 2 F to N-Aryl and N-Alkyl Isocyanates

Key Points

Implication

Abstract

Discussion

Cite This Study

Chemoselective Synthesis of α-Fluoromethyl Amides via the Controlled Addition of LiCH 2 F to N-Aryl and N-Alkyl Isocyanates

Key Points

Implication

Abstract

Discussion

Cite This Study

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