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Review
. 2023 Sep 5;3(6):364-370.
doi: 10.1021/acsorginorgau.3c00029. eCollection 2023 Dec 6.

Synthesis of Fluorinated Amines: A Personal Account

Yi Yang  1 , Alexis Taponard  1 , Julien C Vantourout  1 , Anis Tlili  1
Affiliations
Review

Synthesis of Fluorinated Amines: A Personal Account

Yi Yang et al. ACS Org Inorg Au. .

Abstract

This Account highlights the recent contributions made by our laboratory in the development of novel strategies to synthesize fluorinated amines. These strategies allow the practitioner to efficiently access carbamoyl fluorides, thiocarbamoyl fluorides as well as trifluoromethylamines using CO2 or CS2 as benign C1 sources. In addition, a novel N(SCF3)CF3 moiety was synthesized. Noteworthy, we demonstrated that this reagent could also be used in radical- or electrophilic-based trifluoromethylthiolation reactions.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Current Syntheses of Carbamoyl Fluorides Starting with Amines
Scheme 2
Scheme 2. Synthesis of Carbamoyl Fluorides through Deoxyfluorination of CO2
Scheme 3
Scheme 3. Synthesis of TDAE-SF5–F Reagent
Scheme 4
Scheme 4. Synthesis of Carbamoyl Fluorides through Deoxyfluorination of CO2 with TDAE-SF5–F
Scheme 5
Scheme 5. Current Syntheses of Thiocarbamoyl Fluorides Starting with Amines
Scheme 6
Scheme 6. Synthesis of Carbamoyl Fluorides through Fluorinative Desulfurization of CS2 with DAST
Scheme 7
Scheme 7. Synthesis of Trifluoromethylamines from Thiocarbamoyl Fluorides
Scheme 8
Scheme 8. Synthesis of Thiocarbamoyl Fluorides through Fluorinative Desulfurization of CS2 with TDAE-SF5–F
Scheme 9
Scheme 9. Synthesis of N(SCF3)CF3 Using Munavalli’s Reagent
Scheme 10
Scheme 10. Synthesis of N(SCF3)CF3 Using (SCF3)2 Dimer
Scheme 11
Scheme 11. Trifluoromethylthiolation of Grignard with Reagent 6m
Scheme 12
Scheme 12. Trifluoromethylthiolation of Indole Derivatives with Reagent 6m
Scheme 13
Scheme 13. Synthesis of vinyl-SCF3 under organophotocatalyzed conditions with reagent 6m
Scheme 14
Scheme 14. Synthesis of Aroyl-SCF3 under Organophotocatalyzed Conditions with Reagent 6m
See this image and copyright information in PMC

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