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  4. Christopher Whiteoak

Dr Christopher J Whiteoak MChem, DIC, FHEA, MRSC

Senior Lecturer in Inorganic Chemistry


Summary

Christopher was appointed as a lecturer in Inorganic Chemistry in 2016 having completed his MChem (University of York, 2004), PhD (Imperial College London, 2010) and post-doctoral research positions in France and Spain in the field of catalysis. He teaches Inorganic Chemistry and has an active research programme focusing on the development of new transition metal-catalysed C-H functionalisation protocols and the use of carbon dioxide as a renewable chemical feedstock.

About

After receiving his MChem (University of York) in 2004, Christopher started working for Unilever Research and Development in the laundry research team at their Port Sunlight Research Centre. He obtained a PhD from Imperial College London in 2010 (Supervisors; Prof Vernon C. Gibson and Dr George J. P. Britovsek), after studying in the field of oxidation catalysis. 

Thereafter, he embarked upon an international post-doctoral career, moving to the C2P2 research laboratory at the Ecole Supérieure de Chimie Physique Electronique de Lyon (CPE-Lyon) to carry out research in the field of polymerisation catalysis, under the supervision of Dr Christophe Boisson and Dr Roger Spitz. His work during this period was sponsored by INEOS Olefins and Polymers Europe.

In February 2011, he moved to the group of Prof Arjan W. Kleij at the Institute of Chemical Research of Catalonia (ICIQ), which is established as one of the world's leading catalysis research centres. Here he successfully developed new catalyst systems for the the conversion of carbon dioxide and epoxides into cyclic and polycarbonates. The aluminium catalysts he developed during this period are considered to be amongst the most active for this transformation. 

After completion of this position in 2014, he moved to the QBIS-CAT research group at the Institut de Química Computacional i Catàlisi (IQCC), University of Girona (Dr Xavi Ribas). Here he developed a research project concerning the use of cobalt as catalyst in C-H activation and functionalisation protocols. 

In March 2016 he was appointed as Lecturer in Inorganic Chemistry at Sheffield Hallam University and is now a Senior Lecturer.

Specialist area of interest

Inorganic Chemistry and Catalysis

Teaching

Chris teaches Advanced Inorganic, Physical and Materials Chemistry (Level 6), Physical and Inorganic Chemistry (Level 5), Bio-analytical Methods (Level 4) and Introduction to Inorganic and Materials Chemistry (Level 4)

Research

Development of sustainable chemical conversions through the use of first-row transition metal catalysis

Development of novel C-H functionisation protocols 

                                                                                        
To date, significant progress has been made towards the development of the new C-C and C-X bond forming protocols, with transition metal catalysis leading the field. These advances have offered new routes for significantly shortening and improving the selectivity/reducing waste in multi-step syntheses for the preparation of important pharmaceuticals, natural products and agrochemicals. Historically most success has been achieved with expensive second and third row transition metals, in particular Pd, for which Heck, Negishi and Suzuki were awarded the Nobel Prize for their key contributions in 2010. These Pd protocols require substrates containing halides resulting in significant waste issues in the chemical industry, whereas direct functionalisation of C-H bonds would provide a more atom economic solution and hence greener process. As a result, focus has now shifted towards this more challenging, selective direct functionalisation of ubiquitous C-H bonds. Meanwhile, attention is also turning towards the use of cheaper, more abundant first row transition metals. In this context, Christopher's research seeks to exploit the potential of Co as the basis for novel catalytic and systems for the development of sustainable C-H functionalisation protocols.

Carbon dioxide: a renewable chemical feedstock
    
Carbon dioxide is an interesting carbon feedstock for organic synthesis offering a number of attractive features such as being a renewable, inexpensive and readily available resource. Unfortunately, it is a relatively inert reagent and therefore requires harsh reaction conditions for its activation. In Christopher's research, he focuses on the use of transition metal and organo-catalysis as a way of lowering the high energy barriers in order to provide highly active catalyst systems for the production of value-added products

Collaborators:

Dr Xavi Ribas, University of Girona, Spain.

Publications

Journal articles

Álvarez‐Miguel, L., Burgoa, J.D., Mosquera, M.E.G., Hamilton, A., & Whiteoak, C.J. (2021). Catalytic Formation of Cyclic Carbonates using Gallium Aminotrisphenolate Compounds and Comparison to their Aluminium Congeners: A Combined Experimental and Computational Study. ChemCatChem, 13. http://doi.org/10.1002/cctc.202100910

Henly, E.L., Norris, K., Rawson, K., Zoulias, N., Jaques, L., Chirila, P.G., ... Forbes, S. (2021). Impact of long-term quorum sensing inhibition on uropathogenic Escherichia coli. Journal of Antimicrobial Chemotherapy. http://doi.org/10.1093/jac/dkaa517

Hamilton, A., Wotton, T., Porter, J., Grewal, K., Chirila, P., Forbes, S., ... Whiteoak, C. (2020). Merging Cu-catalysed C-H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles. Organic Chemistry Frontiers. http://doi.org/10.1039/D0QO00283F

Chu, M., Planas, O., Company, A., Ribas, X., Hamilton, A., & Whiteoak, C. (2019). Unravelling the mechanism of cobalt-catalysed remote C-H nitration of 8-aminoquinolinamides and expansion of substrate scope towards 1-naphthylpicolinamide. Chemical Science. http://doi.org/10.1039/c9sc05076k

Kenny, A., Pisarello, A., Bird, A., Chirila, P.G., Hamilton, A., & Whiteoak, C. (2018). A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations. Beilstein journal of organic chemistry, 14, 2366-2374. http://doi.org/10.3762/bjoc.14.212

Chirila, P., Skibinski, L., Miller, K., Hamilton, A., & Whiteoak, C. (2018). Towards a Sequential One-Pot Preparation of 1,2,3-Benzotriazin-4(3H)-ones Employing a Key Cp*Co(III)-catalyzed C-H Amidation Step. Advanced Synthesis & Catalysis, 360 (12), 2324-2332. http://doi.org/10.1002/adsc.201800133

Serrano-Plana, J., Acuña-Parés, F., Dantignana, V., Oloo, W.N., Castillo, E., Draksharapu, A., ... Company, A. (2018). Acid-Triggered O−O Bond Heterolysis of a Nonheme FeIII (OOH) Species for the Stereospecific Hydroxylation of Strong C−H Bonds. Chemistry : A European Journal, 24 (20), 5331-5340. http://doi.org/10.1002/chem.201704851

Chirila, P.G., Adams, J., Dirjal, A., Hamilton, A., & Whiteoak, C. (2018). Cp*Co(III)-Catalyzed coupling of benzamides with α,β-unsaturated carbonyl compounds: Preparation of aliphatic ketones and azepinones. Chemistry : A European Journal, 24 (14), 3584-3589. http://doi.org/10.1002/chem.201705785

Rovira, M., Roldán-Gómez, S., Martin-Diaconescu, V., Whiteoak, C., Company, A., Luis, J., & Ribas, X. (2017). Trifluoromethylation of a well-defined square-planar Aryl-NiII complex involving NiIII/CF3 and NiIV−CF3 intermediate species. Chemistry - A European Journal, 23 (48), 11662-11668. http://doi.org/10.1002/chem.201702168

Chirila, P.G., & Whiteoak, C. (2017). Recent advances using [Cp*Co(CO)I2] catalysts as a powerful tool for C-H functionalisation. Dalton Transactions, 46 (30), 9721-9739. http://doi.org/10.1039/c7dt01980g

Planas, O., Whiteoak, C., Martin-Diaconescu, V., Gamba, I., Luis, J.M., Parella, T., ... Ribas, X. (2016). Isolation of Key Organometallic Aryl-Co(III) Intermediates in Cobalt-Catalyzed C(sp2)–H Functionalizations and New Insights into Alkyne Annulation Reaction Mechanisms. Journal of the American Chemical Society, 138 (43), 14388-14397. http://doi.org/10.1021/jacs.6b08593

Whiteoak, C.J., Planas, O., Company, A., & Ribas, X. (2016). A first example of cobalt-catalyzed remote C-H functionalization of 8-aminoquinolines operating through a single electron transfer mechanism. Advanced Synthesis & Catalysis. http://doi.org/10.1002/adsc.201600161

Planas, O., Whiteoak, C., Company, A., & Ribas, X. (2015). Regioselective Access to Sultam Motifs through Cobalt-Catalyzed Annulation of Aryl Sulfonamides and Alkynes using an 8-Aminoquinoline Directing Group. Advanced Synthesis & Catalysis, 357 (18), 4003-4012. http://doi.org/10.1002/adsc.201500690

Serra, J., Whiteoak, C., Acuña-Parés, F., Font, M., Luis, J.M., Lloret-Fillol, J., & Ribas, X. (2015). Oxidant-Free Au(I)-Catalyzed Halide Exchange and Csp2–O Bond Forming Reactions. Journal of the American Chemical Society, 137 (41), 13389-13397. http://doi.org/10.1021/jacs.5b08756

Corona, T., Pfaff, F.F., Acuña-Parés, F., Draksharapu, A., Whiteoak, C., Martin-Diaconescu, V., ... Company, A. (2015). Reactivity of a Nickel(II) Bis(amidate) Complex withmeta-Chloroperbenzoic Acid: Formation of a Potent Oxidizing Species. Chemistry : A European Journal, 21 (42), 15029-15038. http://doi.org/10.1002/chem.201501841

Taherimehr, M., Sertã, J.P.C.C., Kleij, A.W., Whiteoak, C., & Pescarmona, P.P. (2015). New Iron Pyridylamino-Bis(Phenolate) Catalyst for Converting CO2into Cyclic Carbonates and Cross-Linked Polycarbonates. ChemSusChem, 8 (6), 1034-1042. http://doi.org/10.1002/cssc.201403323

Kleij, A.W., & Whiteoak, C. (2014). Diastereo- and Enantioselective Valorization of Cyclic Organic Carbonates. ChemCatChem, 7 (1), 51-53. http://doi.org/10.1002/cctc.201402801

Martín, C., Whiteoak, C.J., Martin, E., Escudero-Adán, E.C., Galán-Mascarós, J.R., & Kleij, A.W. (2014). Synthesis and structural features of Co(II) and Co(III) complexes supported by aminotrisphenolate ligand scaffolds. Inorganic Chemistry, 53 (21), 11675-11681. http://doi.org/10.1021/ic501883z

Laserna, V., Fiorani, G., Whiteoak, C., Martin, E., Escudero-Adán, E., & Kleij, A.W. (2014). Carbon Dioxide as a protecting group : highly efficient and selective catalytic access to Cycliccis-Diol Scaffolds. Angewandte Chemie International Edition, 53 (39), 10416-10419. http://doi.org/10.1002/anie.201406645

Martín, C., Whiteoak, C., Martin, E., Martínez Belmonte, M., Escudero-Adán, E.C., & Kleij, A.W. (2014). Easily accessible bifunctional Zn(salpyr) catalysts for the formation of organic carbonates. Catalysis Science & Technology, 4 (6), 1615-1621. http://doi.org/10.1039/C3CY01043K

Whiteoak, C., Kielland, N., Laserna, V., Castro-Gómez, F., Martin, E., Escudero-Adán, E.C., ... Kleij, A.W. (2014). Highly active aluminium catalysts for the formation of organic carbonates from CO2 and oxiranes. Chemistry : A European Journal, 20 (8), 2264-2275. http://doi.org/10.1002/chem.201302536

Whiteoak, C., & Kleij, A. (2013). Catalyst development in the context of ring expansion-addition of carbon dioxide to epoxides to give organic carbonates. Synlett, 24 (14), 1748-1756. http://doi.org/10.1055/s-0033-1339483

Whiteoak, C., Henseler, A.H., Ayats, C., Kleij, A.W., & Pericàs, M.A. (2013). Conversion of oxiranes and CO2 to organic cyclic carbonates using a recyclable, bifunctional polystyrene-supported organocatalyst. Green chemistry, 16 (3), 1552-1559. http://doi.org/10.1039/C3GC41919C

Taherimehr, M., Al-Amsyar, S.M., Whiteoak, C., Kleij, A.W., & Pescarmona, P.P. (2013). High activity and switchable selectivity in the synthesis of cyclic and polymeric cyclohexene carbonates with iron amino triphenolate catalysts. Green chemistry, 15 (11), 3083-3090. http://doi.org/10.1039/C3GC41303A

Kielland, N., Whiteoak, C., & Kleij, A.W. (2013). Stereoselective synthesis with carbon dioxide. Advanced Synthesis & Catalysis, 355 (11-12), 2115-2138. http://doi.org/10.1002/adsc.201300422

Whiteoak, C., Nobbs, J.D., Kiryushchenkov, E., Pagano, S., White, A.J.P., & Britovsek, G.J.P. (2013). Tri(pyridylmethyl)phosphine : the elusive congener of TPA shows surprisingly different coordination behavior. Inorganic Chemistry, 52 (12), 7000-7009. http://doi.org/10.1021/ic4005196

Whiteoak, C., Martin, E., Escudero-Adán, E., & Kleij, A.W. (2013). Stereochemical Divergence in the Formation of Organic Carbonates Derived from Internal Epoxides. Advanced Synthesis & Catalysis, 355 (11-12), 2233-2239. http://doi.org/10.1002/adsc.201201070

Whiteoak, C., Kielland, N., Laserna, V., Escudero-Adán, E.C., Martin, E., & Kleij, A.W. (2013). A Powerful Aluminum Catalyst for the Synthesis of Highly Functional Organic Carbonates. Journal of the American Chemical Society, 135 (4), 1228-1231. http://doi.org/10.1021/ja311053h

Whiteoak, C.J., Gjoka, B., Martin, E., Belmonte, M.M., Escudero-Adán, E.C., Zonta, C., ... Kleij, A.W. (2012). Reactivity control in iron(III) amino triphenolate complexes: comparison of monomeric and dimeric complexes. Inorganic Chemistry, 51 (20), 10639-10649. http://doi.org/10.1021/ic3008624

Whiteoak, C., Nova, A., Maseras, F., & Kleij, A.W. (2012). Merging Sustainability with Organocatalysis in the Formation of Organic Carbonates by Using CO2as a Feedstock. ChemSusChem, 5 (10), 2032-2038. http://doi.org/10.1002/cssc.201200255

Taherimehr, M., Decortes, A., Al-Amsyar, S.M., Lueangchaichaweng, W., Whiteoak, C.J., Escudero-Adán, E.C., ... Pescarmona, P.P. (2012). A highly active Zn(salphen) catalyst for production of organic carbonates in a green CO2 medium. Catalysis Science & Technology, 2 (11), 2231-2237. http://doi.org/10.1039/C2CY20171B

Coletti, A., Whiteoak, C., Conte, V., & Kleij, A.W. (2012). Vanadium Catalyzed Synthesis of Cyclic Organic Carbonates. ChemCatChem, 4 (8), 1190-1196. http://doi.org/10.1002/cctc.201100398

Whiteoak, C.J., Martin, E., Belmonte, M.M., Benet-Buchholz, J., & Kleij, A.W. (2012). An efficient iron catalyst for the synthesis of five- and six-membered organic carbonates under mild conditions. Advanced Synthesis & Catalysis, 354 (2-3), 469-476. http://doi.org/10.1002/adsc.201100752

Whiteoak, C.J., Salassa, G., & Kleij, A.W. (2011). Recent advances with π-conjugated salen systems. Chemical Society Reviews, 41 (2), 622-631. http://doi.org/10.1039/c1cs15170c

Whiteoak, C.J., Torres Martin de Rosales, R., White, A.J.P., & Britovsek, G.J.P. (2010). Iron(II) complexes with tetradentate bis(aminophenolate) ligands: synthesis and characterization, solution behavior, and reactivity with O2. Inorganic Chemistry, 49 (23), 11106-11117. http://doi.org/10.1021/ic1016998

Whiteoak, C.J., Britovsek, G.J.P., Gibson, V.C., & White, A.J.P. (2009). Electronic effects in oxo transfer reactions catalysed by salan molybdenum(vi) cis-dioxo complexes. Dalton Transactions, 13, 2337-2344. http://doi.org/10.1039/B820754B

Frantz, S., Wendland, O., Roduner, E., Whiteoak, C.J., & Batchelor, S.N. (2007). Effect of charge on spin probe interaction and dynamics in the nanopores of cotton. Journal of Physical Chemistry C, 111 (39), 14514-14520. http://doi.org/10.1021/jp0754379

Book chapters

Hamilton, A., & Whiteoak, C.J. (2021). Applied organometallics: Cp∗Co(iii)-catalysed C-H functionalisation as a maturing tool for the synthesis of heterocyclic compounds. In Organometallic Chemistry. (pp. 186-228). http://doi.org/10.1039/9781788017077-00186

Planas, O., Whiteoak, C., & Ribas, X. (2019). Recent Advances in Cobalt-Catalyzed Cross-coupling Reactions. In Klein Gebbink, R.J.M., & Moret, M.-.E. (Eds.) Non-noble metal catalysis : molecular approaches and reactions. (pp. 297-328). Wiley-VCH Verlag: http://doi.org/10.1002/9783527699087.ch12

Planas, O., Chirila, P.G., Whiteoak, C., & Ribas, X. (2018). Current mechanistic understanding of Cobalt-Catalyzed C–H functionalization. In Advances in Organometallic Chemistry. (pp. 209-282). Elsevier: http://doi.org/10.1016/bs.adomc.2018.02.002

Postgraduate supervision

Paula Chirila - Development of new methodologies for the synthesis of unusual heterocyclic compounds through the application of cobalt-catalysed C-H functionalisation as a key step.

Maria Distressa Billacura - Development of novel catalytic systems for the application of carbon dioxide as a renewable chemical feedstock.

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