研究领域
Organometallics in organic synthesis
The Stephenson research group is a leader in the field of organoiron mediated organic synthesis, in which the powerful control effects of carbonyliron complexes are brought in to play several times during a synthesis to get complete control of relative and absolute stereochemistry. Major achievements in recent years have the establishment of general regiocontrolled methods to prepare aryl, alkenyl and alkynyl-substitituted cyclohexadienyliron complexes, and new method to enantiomerically pure complexes by the controlled complexation chiral diene ligands available by biotransformations.
Recent industrial support (Industrial Case Award from GSK) has allowed a detailed investigation of dynamic kinetic resolution effects in asymmetric Heck coupling. A strength of the research on organometallics in organic synthesis in Norwich is the capability to address both stoichiometric and catalytic methods.
Current research is supported through the UEA DTA account (studentship to C. Roe) for an organoiron-mediated synthesis of the alkaloid maritidine.
Organometallic bioprobes
The IR vibrational spectra of carbonylmetal complexes are very sensitive to the local environment of the vibrating M-C=O unit, and this has made possible a novel approach to the design of molecular sensors which takes advantage of the narrow band width of the signals to make multiple measurements in a single experiment. IR-based determinations of pH, Li+/Na+/K+ ratios, ?-stacking effects, and protonation/deprotonation events on protein surfaces, have all been established in this work.
Current research is supported in part by the UEA international fund (overseas PhD student: S SudhakaranPillai) and applies these methods to the IR-based detection of sugars and oligosaccharides.
Organometallics for nonlinear optics
The use of organometallics as polarising groups in nonlinear optics has been a collaborative venture coordinated by Stephenson in Norwich through EU COST D4, TMR, COST and D14 programmes, and currently through a COST D26 working group coordinated by Daule in Fribourg.
Current research is supported by EPSRC grant EO/E010490 to facilitate a collaboration with Daule to perform DFT calculations of organometallic dipoles and model compounds. The grant will enable Stephenson to perform DFT calculations in Fribourg, in a research group that is an international leader in the application of DFT to issues in nonlinear optics. Stephenson is also a co-investigator on a grant for nanoscale and molecular photonics at UEA (EPSRC EP/C007751).
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Bulman Page, P., Stephenson, R., Harvey, J., Gaumont, A., Alayrac, C., Slawin, A.(2016)Convenient access to meso benzylic bis-alkynesin Synlett27.pp. A-D Full Text UEA Repository(Article)
Glowacka, P., Stephenson, G.(2016)One-pot synthesis of 9-aminomethylanthracenein Synlett27.pp. 1733-1737 Full Text UEA Repository(Article)
Bulman Page, P. C., Stephenson, G. R., Harvey, J., Slawin, A. M. Z., 1, 2(2016)Ruthenium-Free Preparation of 1,5-Disubstituted Triazoles by Alkylative Debenzylation of 1,4-Disubstituted Triazolesin Synlett27.pp. 2500-2504 Full Text UEA Repository(Article)
Glowacka, P. C., Maindron, N., Richard Stephenson, G., Romieu, A., Renard, P., Emery, F. D. S.(2016)Synthesis and photophysical properties of iron-carbonyl complex-coumarin conjugates as potential bimodal IR-fluorescent probesin Tetrahedron Letters57.pp. 4991–4996 Full Text UEA Repository(Article)
Bew, S. P., Stephenson, G. R., Rouden, J., Ashford, P. A., Bourane, M., Charvet, A., Dalstein, V. M. D., Jauseau, R., Hiatt-Gipson, G. D., Martinez-Lozano, L. A.(2015)Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditionsin Advanced Synthesis & Catalysis357.pp. 1245-1257 Full Text UEA Repository(Article)
Doulcet, J., Stephenson, G. R.(2015)Novel asymmetric formylation of aromatic compounds: Enantioselective synthesis of formyl 7,8- dipropyltetrathia[7]helicenesin Chemistry - A European Journal21.pp. 13431–13436 Full Text UEA Repository(Article)
Doulcet, J., Stephenson, G. R.(2015)The use of (–)-sparteine/organolithium reagents for the enantioselective lithiation of 7,8-dipropyltetrathia[7]helicene: single and double kinetic resolution proceduresin Chemistry - A European Journal21.pp. 18677-18689 Full Text UEA Repository(Article)
Stephenson, G., Cauteruccio, S., Doulcet, J.(2014)Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applicationsin Synlett25.pp. 701-707 Full Text UEA Repository(Article)
Cauteruccio, S., Dova, D., Graiff, C., Carrara, C., Doulcet, J., Stephenson, G. R., Licandro, E., benzo[1, 2-b:4(2014)A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenesin New Journal of Chemistry38.pp. 2241-2244 Full Text UEA Repository(Article)
Stephenson, G., Palotai, I.(2013)Regiodirecting effects in difunctionalised tricarbonyl[(1,2,3,4,5-η)-cyclohexadienyl]iron(1+) salts: building blocks for alkaloidsin Tetrahedron Letters54.pp. 123-127 Full Text UEA Repository(Article)
Stephenson, G. R., Buttress, J., Deschamps, D., Lancelot, M., Martin, J., Sheldon, A., Alayrac, C., Gaumont, A., Bulman Page, P.(2013)An Investigation of the Asymmetric Huisgen 'Click' Reactionin Synlett24.pp. 2723-2729 Full Text UEA Repository(Article)
Bew, S., Stephenson, G., Rouden, J., Martinez-Lozano, L., Seylani, H.(2013)Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enolsin Organic Letters15.pp. 3805-3807 Full Text UEA Repository(Article)
Stephenson, G., Anson, C., Malkov, A., Roe, C.(2012)Influencing the Balance between ipso and ω Nucleophile Addition to (1-Arylcyclohexadienyl)iron Intermediates in Alkaloid Synthesisin European Journal of Organic Chemistry2012.pp. 4716-4732 Full Text UEA Repository(Article)
Monteforte, M., Cauteruccio, S., Maiorana, S., Benincori, T., Forni, A., Raimondi, L., Graiff, C., Tiripicchio, A., Stephenson, G., Licandro, E.(2011)Tetrathiaheterohelicene Phosphanes as Helical-Shaped Chiral Ligands for Catalysisin European Journal of Organic Chemistry2011.pp. 5649-5658 Full Text UEA Repository(Article)
Stephenson, G. R., Anson, C. E., Creaser, C. S., Daul, C. A.(2011)Spectroscopic, Structural and DFT Study of the Responses of Carbonylmetal Crown Ether Complexes to Alkali Metal Cationsin European Journal of Inorganic Chemistrypp. 2086-2097 Full Text UEA Repository(Article)
Stephenson, G. R., Roe, C., Sandoe, E. J.(2011)Electrophilic C-12 Building Blocks for Alkaloids: 1,1 Iterative Organoiron-Mediated Routes to (+/-)-Lycoramine and (+/-)-Maritidinein European Journal of Organic Chemistrypp. 1664-1681 Full Text UEA Repository(Article)
Stephenson, G., Anson, C., Swinson, G.(2011)Biphenyl-cis-diol chemistry to access enantiopure aryl-substituted organoiron complexesin Tetrahedron Letters52.pp. 3547-3550 Full Text UEA Repository(Article)
Roe, C., Sandoe, E. J., Stephenson, G. R.(2010)Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexesin Tetrahedron Letters51.pp. 591-595 Full Text UEA Repository(Article)
Stephenson, G. R., Balfe, A. M., Hughes, D., Kelsey, R. D.(2010)Decomplexation-nitroso Diels-Alder (NDA) approach to C,D-ring functionalisation for hippeastrinein Tetrahedron Letters51.pp. 6806-6809 Full Text UEA Repository(Article)
Bossi, A., Licandro, E., Maiorana, S., Rigamonti, C., Righetto, S., Stephenson, G. R., Spassova, M., Botek, E., Champagne, B.(2008)Theoretical and experimental investigation of electric field induced second harmonic generation in tetrathia 7 helicenesin The Journal of Physical Chemistry C112.pp. 7900-7907 Full Text UEA Repository(Article)
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