Christophe Darcel

Full professor

Email : christophe [dot] darcel [at] univ-rennes1 [dot] fr

Phone : +33 (0) 2 23 23 62 71

Office number : Beaulieu - Build. 10C - 055

Biography

Christophe Darcel studied chemistry at the University of Rennes 1, where he got his PhD in 1995 under the supervision of C. Bruneau and P. H. Dixneuf on ruthenium and palladium catalysed transformations of functional alkynes.  He first spent one year as a postdoctoral fellow in Geneva (Switzerland) with W. Oppolzer working on asymmetric synthesis of natural products using sultam auxiliary. He then obtained a Humboldt fellowship and joined  P. Knochel group in Marburg (Germany) developping chiral zinc derivatives. He was then appointed at the University of Cergy-Pontoise, and at the University of Burgundy as associate professor developing with Sylvain Jugé P-chirogenic ligands and complexes. In 2007, he was appointed full professor at the University of Rennes 1. His current research interests concentrate on homogeneous catalysis with particular emphasis on well-defined iron complexes in catalysis.

Research interest

Homogeneous catalysis with earth abundant transition metals including iron.

  • Catalyzed hydroelementation (Hydrosilylation of carbonyl and carboxylic derivatives, hydroboration of alkenes and alkynes),
  • Iron-catalyzed borylation reaction
  • Iron-catalyzed methylation of amines
  • Novel catalyzed hydrogenation and hydrogen borrowing reactions
  • Ruthenium-catalyzed C-H bond activation
  • New first row transition metal complex and catalyst preparation
  • Asymmetric catalysis and P-chirogenic organophosphorus ligands
  • Oxidation using non noble transitions metals and benign oxidants.

Teaching Activities

Teaching in Licence and Master levels

  • Homogeneous catalysis
  • Organometallic chemistry
  • Organic synthesis
  • Green chemistry

Research interests and selected recent publications

Selected reviews on iron catalysis

- Organophosphorus and Iron Catalysis: Good Partners for Hydrome-talation of Olefins and Alkynes. D. Wei, C. Darcel, J. Org. Chem. 2020, 85, 14298-14306.

- Multi-Step Reactions Involving Iron-Catalysed Reduction and Hydrogen Borrowing Reactions, D. Wei, C. Netkaew, C. Darcel, Eur. J. Inorg. Chem. 2019, 2471-2487.

- Iron-Catalysis in Reduction and Hydrometalation Reactions, D. Wei, C. Darcel, Chem. Rev., 2019, D. Wei, C. Darcel, Chem. Rev. 2019, 119, 2550-2610.

- Non-Noble Metal Catalysis: Molecular Approaches and Reactions, Ed. R. J. Klein Gebbink, M.-E. Moret, Wiley-VCH Verlag GmbH - Iron, cobalt and manganese-catalyzed hydrosilylation of carbonyl compounds and carbon dioxide”, C. Darcel, J.-B. Sortais, D. Wei, A. Bruneau-Voisine, ISBN: 978-3-527-34061-3.

- Iron-catalysed Reduction and Hydroelementation Reactions in Iron CatalysisII Ed. E. Bauer. C . Darcel, J.-B. Sortais, Topics in Organometallic Chemistry 201550, 173-216. 

- When iron met phosphines: a happy marriage for reduction catalysis. L. C. Misal Castro, H. Li, J. B. Sortais, C. Darcel, Green Chem. 2015, 17, 2283-2303.

- Iron-catalysed Cross Dehydrogenative Coupling (CDC) reactions; Editeur: C.-J. Li, RSC Publishing, C-H to C-C bonds: Cross Dehydrogenative Coupling”. C. Darcel, J.-B. Sortais, S. Quintero Duque, 2015, pp 67-92

- N-Heterocyclic Carbene Ligands and Iron: An Effective Association for Catalysis. D. Bézier, J.-B. Sortais, C. Darcel, Adv. Synth. Catal. 2013, 355, 19-33.

Selected  iron catalyzed cascade reduction reactions

- Iron-​Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles. J. Wu, C. Darcel, J. Org. Chem. 202186, 1023-1036.

Iron-​catalyzed hydrosilylation of diacids in the presence of amines: a new route to cyclic amines. D. Wei, C. Netkaew, J. Wu, C. Darcel, ChemCatChem 2020, 12, 5449-5455.

- Iron-Catalysed Reductive Amination of Carbonyl Derivatives with ω-Amino Fatty Acids to Access Cyclic Amines, D. Wei, C. Netkaew, V. Carré, C. Darcel, ChemSusChem 2019, 12, 3008-3012.

- Iron Complexes Catalyzed Switchable Reductive Amination of Levulinic Acid/ Levulinates via Hydrosilylation: Selective Production of Pyrrolidines vs. Pyrrolidinones, D. Wei, C. Netkaew, C. Darcel, Adv. Synth. Catal. 2019, 361, 1781-1786;

- Iron-catalyzed α-Alkylation of Ketones with Alcohols. S. Elangovan, J.-B. Sortais, M. Beller and C. Darcel, Angew. Chem. Int. Ed. 2015, 54, 14483–14486.

- Iron-​catalysed tandem isomerisation​/hydrosilylation reaction of allylic alcohols with amines. H. Li, M. Achard, C. Bruneau, J.-B. Sortais, C. Darcel, RSC Advances 20144, 25892-25897.

Selected  iron catalyzed hydrosilylation reactions

- N-Heterocyclic Carbene Iron Silyl Hydride Complexes, S. Quintero-Duque, H. Li, L. C. Misal Castro, V. Dorcet, T. Roisnel, E. Clot, M. Grellier, J.-B. Sortais, C. Darcel, Isr. J. Chim., 2017, 57, 1216-1221.

- Knölker’s Iron Complexes Bearing a N-heterocyclic Carbene Ligand: Synthesis, Characterization, and Catalytic Dehydration of Primary Amides, S. Elangovan, S. Quintero-Duque, V. Dorcet, T. Roisnel, L. Norel, C. Darcel, J.-B. Sortais, Organometallics 2015, 34, 4521.

- Methylation of Secondary Amines Catalysed by N-Heterocyclic Carbene Piano-Stool Iron Complexes, J. Zheng, C. Darcel, J.-B. Sortais, Chem. Commun. 2014, 50, 14229-14232.

- Cyclopentadienyl)iron(II) Complexes of N-Heterocyclic Carbenes Bearing a Malonate or Imidate Backbone: Synthesis, Structure, and Catalytic Potential in Hydrosilylation V. César, L. C. Misal Castro, T. Dombray, J.-B. Sortais, C. Darcel, S. Labat, K. Miqueu, J.-M. Sotiropoulos, R. Brousses, N. Lugan, G. Lavigne,Organometallics 2013, 32, 4643-4655.

- Selective Reduction of Esters to Aldehydes under the Catalysis of Well-Defined NHC-Iron Complexes, H. Li, L. C. Misal Castro, J. Zheng, T. Roisnel, V. Dorcet, J.-B. Sortais, C. Darcel, Angew. Chem. Int. Ed. 2013, 52, 8045-8049.

- Selective Switchable Iron-Catalyzed Hydrosilylation of Carboxylic Acids. L. C. Misal Castro, H. Li, J.-B. Sortais, C. Darcel, Chem. Commun., 2012, 48, 10514–10516.

- Iron Catalyzed Hydrosilylation of Esters. D. Bézier, G. T. Venkanna, L. C. Misal Castro, J. Zheng, T. Roisnel, J.-B. Sortais, C. Darcel, Adv. Synth. Catal. 2012, 354, 1879-1884.

- Cyclopentadienyl-NHC Iron Complexes for Solvent Free Catalytic Hydrosilylation of Aldehydes and Ketones, D. Bézier, F. Jiang, T. Roisnel, J.-B. Sortais, C. Darcel, Eur. J. Inorg. Chem. 2012, 1333-1337.

- NHC-carbene Cyclopentadienyl Iron Based Catalyst for a General and Efficient Hydrosilylation of Imines. L. C. Misal Castro, J.-B. Sortais, C. Darcel, Chem. Commun. 2012, 48, 151-153.

33. Well-defined Cyclopentadienyl NHC iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles. D. Bézier, G. T. Venkanna, J.-B. Sortais, C. Darcel, ChemCatChem 2011, 3, 1747-1750.

- N-Heterocyclic Carbene Piano-Stool Iron Complexes as Efficient Catalysts for Hydrosilylation of Carbonyl Derivatives, F. Jiang, D. Bézier, J.-B. Sortais, C. Darcel, Adv. Synth. Catal. 2011, 353, 239-244.

Selected  iron catalyzed borylation reactions

- Iron Catalyzed C-H Borylation of Arenes. T. Dombray, C. G. Werncke, S. Jiang, M. Grellier, L. Vendier, S. Bontemps, J.-B. Sortais, S. Sabo-Etienne, C. Darcel, J. Am. Chem. Soc. 2015, 137, 4062.

- Iron-Catalyzed Dehydrogenative Borylation of Terminal Alkynes D. Wei, B. Carboni, J.-B. Sortais, C. Darcel, Adv. Synth. Catal. 2018, 360, 3649-3654.

- (NHC)Fe(CO)4 efficient pre-catalyst for selective hydroboration of alkenes, J. Zheng, J.-B. Sortais, C. Darcel, ChemCatChem, 2014, 6, 763-766.

Selected  3d-metal catalyzed hydrosilylation reactions

- Hydrosilylation of Aldehydes and Ketones Catalyzed by Half-Sandwich Mn(I) N-Heterocyclic Carbene Complexes, J. Zheng, S. Elangovan, D. A. Valyaev, R. Brousses, V. César, J.-B. Sortais, C. Darcel, N. Lugan, G. Lavigne, Adv. Synth. Catal. 2014,  356, 1093-1097.

- Hydrosilylation of imines catalysed by NHC-Nickel catalysts, L. P. Bheeter, M. Henrion, M. J. Chetcuti, C. Darcel, V. Ritleng, J.-B. Sortais, Catal. Sci. Technol. 2013, 3, 3111-3116.

- Cobalt carbonyl based catalyst for hydrosilylation of carboxamides, T. Dombray, C. Helleu, C. Darcel, J.-B. Sortais, Adv. Synth. Catal. 2013, 355, 3358-3362.

- Selective reduction of carboxylic acids to aldehydes through manganese catalysed hydrosilylation, J. Zheng, S. Chevance, C. Darcel, J.-B. Sortais, Chem. Commun. 2013, 49, 10010-10012.

- Hydrosilylation Catalysis of Aldehydes and Ketones by a NHC-Nickel Hydride Complex under Mild Conditions, L. P. Bheeter, M. Henrion, L. Brelot, C. Darcel, M. J. Chetcuti, J.-B. Sortais, V. Ritleng, Adv. Synth. Catal. 2012, 354, 2619-2624.

- Nickel-Catalysed Reductive Amination with Hydrosilanes J. Zheng, T. Roisnel, C. Darcel, J.-B. Sortais, ChemCatChem 2013, 5, 2861-2864. 

- Nickel 1,2,4-triazole based N-heterocyclic carbene complexes: synthesis and catalytic application, L. P. Bheeter, D. Wei, V. Dorcet, T. Roisnel, P. Ghosh, J.-B. Sortais, C. Darcel, Eur. J. Inorg. Chem. 2015, 5226-5231.

Selected  ruthenium catalyzed C-H functionalizations

- Alkenes as hydrogen trappers to control the regio-selective ruthenium(ii) catalyzed ortho C–H silylation of amides and anilides, Q. Lin, Z. Lin, M. Pan, Q. Zheng, H. Li, X. Chen, C. Darcel, P. H. Dixneuf, B. Li, Org. Chem. Front. 2021, doi: 10.1039/D0QO01031F.

- Sp3C–H bond alkylation of ketones with alkenes via ruthenium(II) catalysed dehydrogenation of alcohols, B. Li, C. Darcel, P. H. Dixneuf, Chem. Commun., 2014, 50, 5970-5972.

- Ruthenium(II) -catalysed Functionalisation of C-H Bonds via a Six -membered Cyclometallate: Monoarylation of Aryl 2-pyridyl Ketones, B. Li, C. Darcel, P. H. Dixneuf, ChemCatChem, 2014, 6, 127-130.

- Ruthenium(II) Catalysed Synthesis of Unsaturated Oxazolines via Arene C-H Bond Alkenylation, B. Li ,  K. Devaraj,  C. Darcel, P. H. Dixneuf, Green Chem., 2012, 14, 2706 – 2709.

- Cyclometallation of arylimines and related heterocycles via room-temperature C-H bond activation with acetate-ruthenium(II)-arene complexes, B. Li, C. Darcel, P. H. Dixneuf, Dalton Trans. 2012, 41, 10934 – 10937.

- Sequential Catalysis for the Production of Sterically Hindered Amines: Ru(II)-Catalyzed C_H Bond Activation and Hydrosilylation of Imines, B. Li, C. B. Bheeter, C. Darcel, P. H. Dixneuf, ACS Catal. 2011, 1, 1221-1224.

Labcom GreenCARE (Demeta-UR1-CNRS joint lab)

- Sustainable oxidative cleavage of catechols for the synthesis of muconic acid and muconolactones including lignin upgrading. F. Coupe, L. Petitjean, P. T. Anastas, F. Caijo, V. Escande, C. Darcel, Green Chem. 2020, 22, 6204-6211.

Brevet FR 201858889 déposé le 27/09/2018

Brevet FR 19 01723 déposé le 21/02/2019

Brevet FR 19 10191 déposé le 16/09/2019

Brevet FR 1911863 déposé le 23/10/2019

Brevet FR 19 13526 déposé le 29/11/20019

PUBLICATIONS

 

 

Publications referenced in HAL since 2006