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Literature DB >> 24295125

N-Difluoromethylation of imidazoles and benzimidazoles using the Ruppert-Prakash reagent under neutral conditions.

G K Surya Prakash¹, Sankarganesh Krishnamoorthy, Somesh K Ganesh, Aditya Kulkarni, Ralf Haiges, George A Olah.

Abstract

Direct N-difluoromethylation of imidazoles and benzimidazoles has been achieved using TMS-CF3 (the Ruppert-Prakash reagent) under neutral conditions. Difluoromethylated products were obtained in good-to-excellent yields. Inexpensive, commercially available starting materials, neutral conditions, and shorter reaction times are advantages of this methodology. Reactions are accessible through conventional as well as microwave irradiation conditions.

Entities: Chemical

Year: 2013 PMID： 24295125 DOI： 10.1021/ol403007j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

7 in total

1. Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors: Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2015-09-21 Impact factor: 15.336

2. Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.

Authors: David E Stephens; Gabriel Chavez; Martin Valdes; Monica Dovalina; Hadi D Arman; Oleg V Larionov
Journal: Org Biomol Chem Date: 2014-07-03 Impact factor: 3.876

3. CF₂H, a Hydrogen Bond Donor.

Authors: Chanan D Sessler; Martin Rahm; Sabine Becker; Jacob M Goldberg; Fang Wang; Stephen J Lippard
Journal: J Am Chem Soc Date: 2017-06-27 Impact factor: 15.419

4. ¹⁹F-NMR Diastereotopic Signals in Two N-CHF₂ Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole.

Authors: Diana García-Pérez; Concepción López; Rosa M Claramunt; Ibon Alkorta; José Elguero
Journal: Molecules Date: 2017-11-17 Impact factor: 4.411

N-Difluoromethylation of imidazoles and benzimidazoles using the Ruppert-Prakash reagent under neutral conditions.

1. Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

2. Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.

3. CF₂H, a Hydrogen Bond Donor.

4. ¹⁹F-NMR Diastereotopic Signals in Two N-CHF₂ Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole.

5. Insertion of Carbenes into Deprotonated nido-Undecaborane, B₁₁H₁₃(2-).

Review 6. Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C-C Bonds.

7. Synthesis of purines and adenines containing the hexafluoroisopropyl group.

N-Difluoromethylation of imidazoles and benzimidazoles using the Ruppert-Prakash reagent under neutral conditions.

1. Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

2. Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides.

3. CF2H, a Hydrogen Bond Donor.

4. 19F-NMR Diastereotopic Signals in Two N-CHF₂ Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole.

5. Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-).

Review 6. Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C-C Bonds.

7. Synthesis of purines and adenines containing the hexafluoroisopropyl group.

3. CF₂H, a Hydrogen Bond Donor.

4. ¹⁹F-NMR Diastereotopic Signals in Two N-CHF₂ Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole.

5. Insertion of Carbenes into Deprotonated nido-Undecaborane, B₁₁H₁₃(2-).