NORMAND Adrien Voir la fiche profil en français

2016: CNRS research associate, ICMUB.
2012-2016: Postdoc / Temporary lecturer, Université de Bourgogne (Pr P. Le Gendre) and WWU Münster (Pr G. Erker).
2009-2012: Research portfolio manager (« sustainable chemistry » programmes), Agence Nationale de la Recherche (Pr P. Cognet).
2008-2009: Postdoc, University of Ottawa (Pr D. Fogg).
2007-2008: Industrial postdoc, Sanofi-Aventis (P. Mailliet), Vitry-sur-Seine.
2007: PhD in chemistry, Cardiff University (Pr K. J. Cavell).

I am interested in the chemistry of transition metals and main group elements (included, but not limited to, titanium and phosphorus). Particular emphasis is placed on:

• ü The synthesis and characterisation of organometallic compounds.
• ü  The elucidation of questions pertaining to the nature of metal-ligand interactions: links between experiments and theory, epistemological implications (what is a chemical bond?).
• ü  Reactivity studies, notably in small molecule activation (H₂, CO₂, P₄).
• ü  Applications to catalysis.

Current projects:

Current research is focussed on:
1. Catalytic applications of group 4 amido- and phosphidometallocene cations (see our paper)

2. Synthetic applications of reactive bis(iminophosphoranyl)phosphide (BIPP) ligands (see our papers here and here).

Papers in peer-reviewed journals (*: corresponding author):
16. "Template synthesis of NPN' pincer-type Ligands at Titanium using an ambiphilic phosphide scaffold" A. Moerman, E. D. Sosa Carrizo, B. Théron, H. Cattey, P. Le Gendre, P. Fleurat-Lessard* and A. T. Normand*, Inorg. Chem., 2022, 61, 7642-7653.
15. "Coordinatively unsaturated amidotitanocene cations with inverted σ and π bond strengths: controlled release of aminyl radicals and hydrogenation/dehydrogenation catalysis" Q. Bonnin, T. Edlová, E.-D. Sosa Carrizo*, P. Fleurat-Lessard, H. Cattey, P. Richard, P. Le Gendre* and A. T. Normand*, Chem. Eur. J., 2021, 27, 18175-18187.
14. "Reappraising Schmidpeter's bis(iminophosphoranyl)phosphides: coordination to metals and bonding analysis", A. T. Normand*, E.-D. Sosa Carrizo*, C. Magnoux, E. Lobato, H. Cattey, P. Richard, S. Brandès, C. H. Devillers, A. Romieu, P. Le Gendre and P. Fleurat-Lessard, Chem. Sci., 2021, 12, 253-269.
13. "Phosphasalen group IV metal complexes: synthesis, characterization and ring opening polymerization of lactide" A. T. Normand, R. Malacea-Kabbara, R. Lapenta, A. Dajnak, P. Richard, H. Cattey, A. Bolley, A. Grassi, S. Milione, A. Auffrant,* S. Dagorne* and P. Le Gendre*, Dalton Trans. 2020, 49, 6980-7004.
12. "The taming of redox-labile phosphidotitanocene cations"A. T. Normand*, Q. Bonnin, S. Brandès, P. Richard, P. Fleurat-Lessard, C. H. Devillers, C. Balan, P. Le Gendre,* G. Kehr and G. Erker, Chem. Eur. J., 2019, 25, 2803-2815.
11. "A Route toward (Aminomethyl)cyclopentadienide Ligands and Their Group 4 Metal Complexes" Quentin Bonnin, Sook‐Yen Wong, Cédric Balan, Virginie Comte, Raluca Malacea, Marie‐José Penouilh, Philippe Richard, Gerald Kehr, Adrien T. Normand, Gerhard Erker* and Pierre Le Gendre*, Eur. J. Inorg. Chem., 2018, 3813-3821.
10. "Direct P-functionalization of azobenzene by a cationic phosphidozirconocene complex" A. T. Normand*, C. G. Daniliuc, G. Kehr, P. Le Gendre and G. Erker, Dalton Trans., 2016, 3711-3714.
9. "Insertion reactions of neutral phosphidozirconocene as a convenient entry into frustrated Lewis pair territory" A. T. Normand*, C. G. Daniliuc, B. Wibbeling, G. Kehr, P. Le Gendre* and G. Erker, Chem. Eur. J., 2016, 22, 4285-4293.
8. "Phosphido- and amidozirconocene cation-based frustrated Lewis pair chemistry" A. T. Normand, C. G. Daniliuc, B. Wibbeling, G. Kehr, P. Le Gendre* and G. Erker*, J. Am. Chem. Soc., 2015, 137, 10796-10808.
7. "Synthetic endeavors towards titanium based frustrated Lewis pairs with controlled steric and electronic properties" A. T. Normand, P. Richard, C. Balan, C. G. Daniliuc, G. Kehr, G. Erker* and P. Le Gendre*, Organometallics, 2015, 34, 2000-2011.
6. "Titanium imido complexes stabilised by bis(iminophosphoranyl)methanide ligands: the influence of N-substituents on solution dynamics and reactivity" A. T. Normand, A. Massard, P. Richard, C. Canovas, C. Balan, M. Picquet, A. Auffrant* and P. Le Gendre*, Dalton Trans., 2014, 15098-15110.
5. "N-heterocyclic carbenes bearing two, one and no nitrogen atoms at the ylidene carbon: insight from theoretical calculations" A. A. Tukov, A. T. Normand* and M. S. Nechaev*, Dalton Trans., 2009, 7015-7028.
. "Mechanisms in the reaction of palladium(II)–π-allyl complexes with aryl halides: evidence for NHC exchange between two palladium complexes" A. T. Normand, M. S. Nechaev* and K. J. Cavell*, Chem. Eur. J., 2009, 15, 7063-7073.
3. "Design of cationic mixed phosphine/N-Heterocyclic Carbene palladium(II) π -allyl complexes as monoligated phosphine Pd(0) precatalysts: synthesis, structural studies, catalysis, and reactivity" A. T. Normand, A. Stasch, L.-L. Ooi and K. J. Cavell*, Organometallics, 2008, 27, 6507-6520.
2. "Catalytic annulation of heterocycles via a novel redox process Involving the imidazolium salt N-Heterocyclic carbene couple" A. T. Normand, S. K. Yen, H. V. Huynh*, T. S. A. Hor and K. J. Cavell*, Organometallics, 2008, 27, 3153-3160.
1. "Atom-efficient catalytic coupling of imidazolium salts with ethylene involving Ni-NHC complexes as intermediates: a combined experimental and DFT study" A. T. Normand, K. J. Hawkes, N. D. Clement, K. J. Cavell* and B. F. Yates*, Organometallics, 2007, 26, 5352-5363.

Review:
1. "Donor-functionalised N-Heterocyclic Carbene Complexes of group 9 and 10 metals in catalysis: trends and directions" A. T. Normand and K.J. Cavell*, Eur. J. Inorg. Chem., 2008, 2781-2800.

Other paper:
1. "Chimie verte — la technoscience au pied de l'arc-en-ciel" Adrien Normand*, Vocabulaire Spéculatif et Critique des Transitions, 2021 (invited article in French, https://vocabulairedestransitions.fr/article-18).

Patent:
1. "New platinum complexes obtained by reacting platinum compound and amine compound, useful as anticancer agent" FR2954321(A1). (Sanofi-Aventis)

Book Chapters:
1. "N-heterocyclic and mesoionic carbene complexes of the group 4 metals" in Comprehensive Organometallic Chemistry IV; eds G. Parkin, K. Mayer, D. O'Hare; Elsevier: Oxford, to be published in 2022 (DOI: 10.1016/B978-0-12-820206-7.00003-2).
2. "NHC-palladium complexes in catalysis", A. T. Normand and K. J. Cavell* in N-heterocyclic carbenes: from laboratories curiosities to efficient synthetic tools, ed. S. Díez-González, Royal Society of Chemistry, 2011 (1^st edition), (2016 2^nd edition).
3. "Deactivation pathways of NHCs", A. T. Normand and K. J. Cavell* in Heterocyclic carbenes in transition metal catalysis and organocatalysis, ed. C. S. J. Cazin, Springer, 2011.

Présentations orales :
JCC 2022, Lille 2022 | Journées des CR de l’INC, Meudon 2021 ┃ JCC 2016, Toulouse 2016 ┃ ICOMC XXVII, Melbourne (Australie) 2016 ┃ ASMOS X, Dijon 2014 ┃ ASMOS IX, Münster (Allemagne) 2013 | LCC Toulouse 2009 (invitation du Dr G. Lavigne) ┃ Cardiff Easter conference 2007

Présentations par affiches :
JCC 2018, Brest 2018 ┃ Autumn school INSPECTHE, Autrans 2018 | 92nd CSC, Hamilton (Canada) 2009 ┃ ICOMC XXII, Zaragoza (Spein) 2006 ┃ ICOMC XXIII, Rennes 2008

Vulgarisation :

I was the guest of the radio show « Quoi de Neuf Chercheur ? » aired in septembre 2019 on Radio Dijon Campus (FM 92.2). The complete recording is available on HAL.

I am a synthetic chemist, an organic “monkey” by training. Over the years, I have shifted my research towards coordination chemistry. My “core business” lies in the handling of species that are sensitive to laboratory conditions (oxygen, water, light, heat), including pyrophoric compounds: white phosphorus (P₄), silane gas (SiH₄), neat trimethylaluminium and the like.

I am one of a few chemists in Europe who has mastered the allotropic conversion of phosphorus as originally reported by Baker at the end of the XIXth century. For an adaptation of this procedure, see the supporting information of our paper (Chem. Sci. 2021, 12, 253).

DISCLAMER: the procedure outlined below is for illustration purposes only, see the full text of the publication for the complete procedure together with hazards assessment.

Step 1: beginning of thermolysis. The heatgun is placed underneath the pile of red phosphorus. Note that the Schlenk tube is placed under static vacuum and lubricated with Apiezon H grease.	Step 2: after a few minutes, white phosphorus condenses on the cooler parts of the Schlenk tube. The heatgun is progressively moved towards the bottom end of the tube (right).
Step 3: after cooling and transfer in the glovebox, the Schlenk tube is scraped and the solids are extracted with CH2Cl2 in an ordinary Schlenk flask lubricated with Dow Corning Si grease.	Step 4: after overnight extraction, the solids are filtered over a grade 4 glass frit in the glovebox. Note that for this batch, residual lumps of P4 can be observed. A second extraction was necessary in order to completely separate P4 from red phosphorus.
Step 5: the CH2Cl2 solution is evaporated to dryness with a vacuum line.	Step 6: finely divided P4 is obtained after collection in the glovebox.
Step 7: residues of P4 are burned under a flow of air. Note that this step is performed with the sash of the fumehood completely lowered, in order to protect the operator from toxic PxOy fumes. A larger metal pan may also be used as a protection from airborne burning P4 particles if required. The glassware may then be cleaned with water and cleaning powder.	Step 8: the Schlenk tube can now be cleaned safely.

2020-2022 (uB):
Elected member of the “Commission de la Recherche” (Université de Bourgogne, Dijon). University Senate with 40 members, in charge of funding attribution, local promotion of University staff etc.

2009-2012 (ANR):
Management of research funding programmes (92 projects, total budget 45M€): this position consisted in following the administrative and scientific aspects of research projects funded by the ANR within the framework of its interdisciplinary “sustainable chemistry” programmes (CP2D and CD2I).
Coordination of the selection process of the proposals submitted to ANR, organization and management of the selection committees, solicitation of external reviewers.
Moderation of the working group “Consequences of the application of REACH for polymers” organised jointly with ANR and the French Chemical Society (SCF). See l’Actualité Chimique, 2012, 4-7.
Organization of the “ANR Sustainable Chemistry Conference”, 18-19th September 2012, Lyon, France (http://www.agence-nationale-recherche.fr/Colloques/CD2012/). (> 160 participants)