Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents
Abstract
:1. Introduction
2. C Fragment
3. CH Fragment
- -
- pyrimidines from t-BuOOH-mediated reaction between acetophenones, amidines and DMF (Equation (15)) [47],
- -
- substituted phenols also from three components cycloadditions (Equation (16)) [48],
- -
- 3-acylindoles from 2-alkenylanilines (Equation (17)) [49],
- -
- benzimidazoles and benzothiazole from o-phenylenediamine or 2-aminobenzenethiol through carbon dioxide-mediated cyclization (Equation (18)) [50].
4. CH2 Fragment
5. NC Fragment
6. NMe2 Fragment
6.1. Aryl Halides
6.2. Alkylarenes
6.3. Alkenes
6.4. Acids
- -
- the amidation of acids promoted with propylphosphonic anhydride associated to HCl at 130 °C (Equation (36)) [15],
- -
- the amination of acids employing a hypervalent iodine reagent at room temperature (Equation (37)) [35]. Mesityliodine diacetate was superior to the other hypervalent iodine reagents, while oxidants such as I2, t-BuOOH, NaIO4 or K2S2O8 did not mediate the amidation reaction [35].
6.5. Carbonylated Compounds
6.6. Benzyl Amines
6.7. Nitriles
6.8. Sulfur Compounds
7. O Fragment
8. C=O Fragment
- -
- via C(sp2)-H bond activation and annulation using Pd/C [67] or Pd(OAc)2 [8], in the presence of K2S2O8, CF3CO2H and O2 (Equation (53)),or carbon dioxide-mediated cyclization of 2-aminobenzonitrile (Equation (54)) [50]. This latter reaction would involve a Vilsmeier-Haack type intermediate and did not occur with DMAc.
9. C=ONMe2 Fragment
10. H Fragment
11. RC Fragment
12. RCNMe2 Fragment
13. RC-O Fragment
14. RC=O Fragment
15. RC=ON(CH2)Me Fragment
16. HC-ONMe2 Fragment
17. RC and O Fragment
18. RCNMe2 and O Fragment
19. HC=O and HC Fragment
20. H and NMe2 Fragment
21. H and C=ONMe2 Fragment
22. H, C=ONMe2 and NMe2 Fragment
23. C=ONMe2 and CH Fragment
24. Reducing or Stabilizing Agent
- -
- on iron for the hydrosilylation of alkenes (Equation (103)) [109],
- -
- on palladium for the synthesis of 2,3-disubstituted indoles from 2-halooanilines and alkynes (Equation (104)) [110],
- -
- on copper for Sonogashira–Hagihara cross-coupling reactions (Equation (105)) [111],
- -
- on iridium for methylation of alcohols (Equation (106)) and amines (Equation (107)), using methanol as the C1 source [112].
25. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Le Bras, J.; Muzart, J. Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents. Molecules 2018, 23, 1939. https://doi.org/10.3390/molecules23081939
Le Bras J, Muzart J. Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents. Molecules. 2018; 23(8):1939. https://doi.org/10.3390/molecules23081939
Chicago/Turabian StyleLe Bras, Jean, and Jacques Muzart. 2018. "Recent Uses of N,N-Dimethylformamide and N,N-Dimethylacetamide as Reagents" Molecules 23, no. 8: 1939. https://doi.org/10.3390/molecules23081939