Diazo chemistry

Fluorine chemistry


Emerging Applications of Aryl Trifluoromethyl Diazoalkanes and Diazirines in Synthetic Transformations

Ollevier, T.; Carreras, V. ACS Org. Inorg. Au 2022, in press. doi: 10.1021/acsorginorgau.1c00027.


Fluoride-triggered Synthesis of 1-Aryl-2,2-Difluoroalkenes via Desilylative Defluorination of (1-Aryl)-2,2,2-trifluoroethyl-silanes

Carreras, V.; Ollevier, T. J. Org. Chem. 2021, 86, 13160–13168. doi: 10.1021/acs.joc.1c01724.


Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow

Tanbouza, N.; Carreras, V.; Ollevier, T. Org. Lett. 2021, 23, 5420–5424. doi: 10.1021/acs.orglett.1c01750.


Asymmetric CuI-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si-H Bonds

Carreras, V.; Besnard, C.; Gandon, V; Ollevier, T. "Asymmetric CuI-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si-H Bonds", Org. Lett. 2019, 21,9094–9098. doi: 10.1021/acs.orglett.9b03480.

Iron chemistry


Iron-Catalyzed Carbene Insertion Reactions of α-Diazoesters into Si-H Bonds

Tanbouza, N.; Keipour, H.; Ollevier, T. "FeII-Catalysed Insertion Reaction of α-Diazocarbonyls into X-H Bonds (X = Si, S, N, and O) in Dimethyl Carbonate as a Suitable Solvent Alternative", RSC Advances 2019, 9, 31241–31246. doi: 10.1039/c9ra07203a.

Copper chemistry


Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds"

Keipour, H.; Jalba, A.; Delage-Laurin, L.; Ollevier, T. "Copper-Catalyzed Carbenoid Insertion Reactions of α-Diazoesters and α-Diazoketones into Si-H and S-H Bonds", RSC Advances 2017, 82, 3000–3010. doi: 10.1021/acs.joc.6b02998.

Asymmetric catalysis

Ligand design


C2-Symmetric 2,2'-Bipyridine-α,α'-1-adamantyl-diol Ligand: Bulky Iron-Complexes in Asymmetric Catalysis

Lauzon, S.; Ollevier, T. Org. Lett. 2022, 24. doi: 10.1021/acs.orglett.2c00141.


2,2'-Bipyridine-α,α'-trifluoromethyl-diol ligand: synthesis and application in the asymmetric Et2Zn alkylation of aldehydes

Lauzon, S.; Ollevier, T. Chem. Commun. 2021, 57, 11025–11028. doi: 10.1039/d1cc04556c.


Iron catalysis


Efficient stereoselective synthesis of chiral 3,3'- dimethyl-(2,2'-bipyridine)-diol ligand and applications in FeII-catalysis

Lauzon, S.; Caron, L.; Ollevier, T. Org. Chem. Front. 2021. doi: 10.1039/d1qo00188d.


Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives

Lauzon, S.; Keipour, H.; Gandon, V.; Ollevier, T. "Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives", Org. Lett. 2017, 19, 6324-6327. doi: 10.1021/acs.orglett.7b03118. Highlighted in Synfacts:"Iron(II)-Catalyzed Michael Addition" , Lautens, M. ; Zeidan, N. Synfacts 2018, 158.

Bismuth catalysis


Bismuth Triflate-catalyzed Asymmetric Allylation of Aromatic Aldehydes

Li, Z.; Plancq., B.; Ollevier, T. "Bismuth Triflate-catalyzed Asymmetric Allylation of Aromatic Aldehydes", Chem. Eur. J. 2012, 18, 3144–3147.

Electrosynthesis

Anodic oxidation


Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

Leech, M. C.; Petti, A.; Tanbouza, N.; Mastrodonato, A.; Goodall, I. C. A.; Ollevier, T.; Dobbs, A.; Lam, K. Org. Lett. 2021, 23, 9371–9375. doi: 10.1021/acs.orglett.1c03475.


Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

Petti, A.; Fagnan, C.; van Melis, C.; Tanbouza, N.; Garcia, A.; Mastrodonato, A.; Leech, M.; Goodall, I.; Dobbs, A.; Ollevier, T.; Lam, K. Organic Process Research & Development 2021, 25, 2614–2621. doi: 10.1021/acs.oprd.1c00112.


Metal-free chemistry

Hydroamination reactions


Hydrogen Bond-Promoted Metal-Free Hydroamination of Alkynes

Bahri, J.; Tanbouza, N.; Ollevier, T. Synlett 2019, 30, 2086-2090. doi: 10.1055/s-0039-1690988.


Arylation reactions


Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones

Zaid, Y.; Mboyi, C. D.; Pichette Drapeau, M.; Radal, L.; Ouazzani Chahdi, F; Kandri Rodi, Y; Ollevier, T.; Taillefer, M. ""Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones"", Chem. Eur. J. 2018, 24, 17449–17453. doi:10.1002/chem.201804415.

Oxaziridine synthesis


Hydrogen peroxide/dimethyl carbonate: a green system for epoxidation of N-alkylimines and N-sulfonylimines. One-pot synthesis of N-alkyloxaziridines from N-alkylamines and (hetero)aromatic aldehydes

Kraïem, J.; Ghedira, D.; Ollevier, T. "Hydrogen peroxide/dimethyl carbonate: a green system for epoxidation of N-alkylimines and N-sulfonylimines. One-pot synthesis of N-alkyloxaziridines from N-alkylamines and (hetero)aromatic aldehydes", Green Chem. 2016, 18, 4859–4864. doi: 10.1039/c6gc01394e.

NHC chemistry

Diels-Alder reaction


Recyclable Iron(II) Caffeine-derived Ionic Salt Catalyst in the Diels-Alder Reaction of Cyclopentadiene and α,β-Unsaturated N-Acyl-oxazolidinones in Dimethyl Carbonate

Meng, D.; Li, D.; Ollevier, T. "Recyclable Iron(II) Caffeine-derived Ionic Salt Catalyst in the Diels-Alder Reaction of Cyclopentadiene and α,β-Unsaturated N-Acyl-oxazolidinones in Dimethyl Carbonate", RSC Advances 2019, 9, 21956–21963. doi: 10.1039/c9ra04098f.

Synthesis of biologically-active molecules

Synthesis of dihydroquinoxazolinones


Iron- and Zinc-mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones

Li, D.; Ollevier, T. "Iron- and Zinc-mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones", Eur. J. Org 2019, 9, 1273–1280. doi: 10.1002/ejoc.201801639.