Diazo chemistry

Fluorine chemistry

Fluorine in metal-catalyzed asymmetric transformations: the lightest halogen causing a massive effect

Lauzon, S.; Ollevier, T. Chem. Sci. 2022, in press. doi: 10.1039/d2sc01096h.

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 Cu^I-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si–H Bonds

Carreras, V.; Besnard, C.; Gandon, V; Ollevier, T. Org. Lett. 2019, 21,9094–9098. doi: 10.1021/acs.orglett.9b03480.

Iron chemistry

The Power of Iron Catalysis in Diazo Chemistry

Carreras, V.; Tanbouza, N.; Ollevier, T. Synthesis 2021, 53,79–94. doi: 10.1055/s-0040-1707272. This article is editor's choice.

Fe^II-Catalysed Insertion Reaction of α-Diazocarbonyls into X–H Bonds (X = Si, S, N, and O) in Dimethyl Carbonate as a Suitable Solvent Alternative

Tanbouza, N.; Keipour, H.; Ollevier, T. RSC Advances 2019, 9, 31241–31246. doi: 10.1039/c9ra07203a.

α-Thiocarbonyl Synthesis via Fe^II-Catalyzed Insertion Reaction of α-Diazocarbonyls into S–H Bonds

Keipour, H.; Jalba, A.; Tanbouza, N.; Carreras, V.; Ollevier, T. Org. Biomol. Chem. 2019, 17, 3098–3102. This article is part of the themed collections: "Synthetic methodology in OBC" and "Carbenes in Organic Synthesis". doi: 10.1039/c9ob00261h.

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. J. Org. Chem. 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 Fe^II-catalysis

Lauzon, S.; Caron, L.; Ollevier, T. Org. Chem. Front. 2021, 8, 2242–2249. doi: 10.1039/d1qo00188d.

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

Lauzon, S.; Keipour, H.; Gandon, V.; Ollevier, T. 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.

Asymmetric Diels-Alder Reaction of α,β-Unsaturated Oxazolidin-2-one Derivatives Catalyzed by a Chiral Fe(III)-Bipyridine Diol Complex

Li, M.; Carreras, V.; Jalba, A.; Ollevier, T. Org. Lett. 2018, 20, 995–998. doi: 10.1021/acs.orglett.7b03939.

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.

Sulfoxide chemistry

Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability

Vroemans, R.; Ribone, S.; Thomas, J.; Van Meervelt, L.; Ollevier, T.; Dehaen, W. Org. Biomol. Chem. 2021, 19, 6521–6526. doi: 10.1039/D1OB00784J.

Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution using Aqueous H2O2 and Chiral Iron Bis(oxazolinyl)bipyridine Catalysts

Jalba, A.; Régnier, N.; Ollevier, T. Eur. J. Org. Chem. 2017, 1628–1637. doi: 10.1002/ejoc.201601597.

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/vinylation 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. Chem. Eur. J. 2018, 24, 17449–17453. doi:10.1002/chem.201804415.

Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes

Zaid, Y.; Mboyi, C. D.; Pichette Drapeau, M.; Radal, L.; Ouazzani Chahdi, F; Kandri Rodi, Y; Ollevier, T.; Taillefer, M. Org. Lett. 2019, 21, 1564–1568. doi: 10.1021/acs.orglett.8b04004.

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

Pichette Drapeau, M.; Tlili, A.; Zaid, Y.; Toummini, D.; Ouazzani Chahdi, F.; Sotiropoulos, J.-M.; Ollevier, T. 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. Green Chem. 2016, 18, 4859–4864. doi: 10.1039/c6gc01394e.

Synthesis of biologically-active molecules

Synthesis of dihydroquinoxazolinones

Iron- and Zinc-mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones

Li, D.; Ollevier, T. Eur. J. Org 2019, 9, 1273–1280. doi: 10.1002/ejoc.201801639.

NHC chemistry

Cu NHC

Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air

Li, D.; Ollevier, T. J. Organomet. Chem. 2020, 906, 121025. doi: 10.1016/j.jorganchem.2019.121025.

Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air

Li, D.; Ollevier, T. Org. Lett. 2019, 21, 3572. doi: 10.1021/acs.orglett.9b00973.

Heterogeneous catalysis

Iron-catalyzed Mukaiyama aldol reaction

Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction

Wan, X.; Ollevier, T.; Kleitz, F. ACS Catal. 2018, 8, 1932–1944. doi: 10.1021/acscatal.7b03485.

Green engineering

Valorization of biomass

Bio-char as an Additive to Modify Bio-pitch Binder for Carbon Anodes

Lu, Y.; Hussein, A.; Lauzon-Gauthier, J.; Ollevier, T.; Alamdari, H. ACS Sustainable Chem. Eng. 2021, 9. doi: 10.1021/acssuschemeng.1c04941.

Properties of Bio-pitch and its Wettability on Coke

Lu, Y.; Hussein, A.; Li, D.; Huang, X.; Mollaabbasi, R.; Picard, D.; Ollevier, T.; Alamdari, H. ACS Sustainable Chem. Eng. 2020, 8, 15366–15374.

Synthesis and Characterization of Bio-pitch from Bio-oil

Lu, Y.; Li, D.; Huang, X.; Picard, D.; Mollaabbasi, R.; Ollevier, T.; Alamdari, H. ACS Sustainable Chem. Eng. 2020, 8, 11772–11782. doi: 10.1021/acssuschemeng.0c03903.

Diazo chemistry

Fluorine chemistry

Fluorine in metal-catalyzed asymmetric transformations: the lightest halogen causing a massive effect

Emerging Applications of Aryl Trifluoromethyl Diazoalkanes and Diazirines in Synthetic Transformations

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

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

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

Iron chemistry

The Power of Iron Catalysis in Diazo Chemistry

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

α-Thiocarbonyl Synthesis via FeII-Catalyzed Insertion Reaction of α-Diazocarbonyls into S–H Bonds

Copper chemistry

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

Asymmetric catalysis

Ligand design

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

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

Iron catalysis

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

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

Asymmetric Diels-Alder Reaction of α,β-Unsaturated Oxazolidin-2-one Derivatives Catalyzed by a Chiral Fe(III)-Bipyridine Diol Complex

Bismuth catalysis

Bismuth Triflate-catalyzed Asymmetric Allylation of Aromatic Aldehydes

Sulfoxide chemistry

Synthesis of homochiral sulfanyl- and sulfoxide-substituted naphthyltriazoles and study of the conformational stability

Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution using Aqueous H2O2 and Chiral Iron Bis(oxazolinyl)bipyridine Catalysts

Electrosynthesis

Anodic oxidation

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

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

Metal-free chemistry

Hydroamination reactions

Hydrogen Bond-Promoted Metal-Free Hydroamination of Alkynes

Arylation/vinylation reactions

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

Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes

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

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

Synthesis of biologically-active molecules

Synthesis of dihydroquinoxazolinones

Iron- and Zinc-mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones

NHC chemistry

Cu NHC

Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air

Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air

Heterogeneous catalysis

Iron-catalyzed Mukaiyama aldol reaction

Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction

Green engineering

Valorization of biomass

Bio-char as an Additive to Modify Bio-pitch Binder for Carbon Anodes

Properties of Bio-pitch and its Wettability on Coke

Synthesis and Characterization of Bio-pitch from Bio-oil

Asymmetric Cu^I-Catalyzed Insertion Reaction of 1-Aryl-2,2,2-trifluoro-1-diazoethanes into Si–H Bonds

Fe^II-Catalysed Insertion Reaction of α-Diazocarbonyls into X–H Bonds (X = Si, S, N, and O) in Dimethyl Carbonate as a Suitable Solvent Alternative

α-Thiocarbonyl Synthesis via Fe^II-Catalyzed Insertion Reaction of α-Diazocarbonyls into S–H Bonds

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

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

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

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