Professor Ian Fairlamb

01904 324091
Email: ian.fairlamb@york.ac.uk

Catalysis: reactivity, mechanism and application (chemical biology and target-orientated synthesis)

Our core interests are in the development and application of transition metal chemistry in catalysis and synthetic chemistry.  We are particularly interested in metal catalyst design and mechanistic understanding, especially in C-H and C-X activation processes, which we have a strong track record in.  Our work has links to chemical biology, supported by collaboration with others. Organometallic therapeutic agents such as carbon monoxide releasing molecules and fluorescent heteroaromatic compounds (purines and 2-pyrones) are of interest to the research group. Finally, we are engaged in some natural product synthesis, e.g. macrocyclic terpene derived compounds, which acts as a sharpening tool for our new catalysts and catalytic processes.

For information relating to new research projects (e.g. PhD, masters etc.) and Group Information (PDF  , 693kb) - click here

Latest paper just accepted:

"A mild and selective Pd-mediated methodology for the synthesis of highly fluorescent 2-arylated tryptophans and tryptophan-containing peptides: a catalytic role for Pd0 nanoparticles?"

T. J. Williams, A. J. Reay, A. C. Whitwood, I. J. S. Fairlamb, Chem. Commun., 2014, DOI:10.1039/C3CC48481E.

In this paper we show how Pd nanoparticles are formed in a C-H bond functionalisation reaction {generated from Pd(OAc)2}. Moreover, we show that Pd nanoparticles stabilised by a PVP polymer, can mediate a selective C-H bond functionalisation reaction.  A series of fluorescent 2-aryl-tryptophans have been prepared and characterised, which hold promise as non-natural amino acids.

On-going research projects

1) Metal-alkene interactions in transition metal catalysis, particularly palladium mediated cross-coupling processes.

Scheme of Metal Alkene Interactions

2) Exploiting pseudohalide effects in transition metal catalysis.

Scheme of Exploiting Pseudohalides

3) Ligand design in metal catalysis (including biotransformations).

Scheme of Ligand Design

4) Unusual observations in metal-mediated processes.

Scheme of Unusual Observations

5) CO releasing molecules and functionalised heteroaromatic therapeutic agents

Scheme of CO releasing molecules

6) Catalytically relevant metal-containing nanoparticles in C-H and C-X bond-forming processes.

Scheme of Nanoparticles

7) Target-orientated synthesis interests.

Scheme of target-directed synthesis

8) C-H activation of purines (adenosine and guanosine): new fluorescent / therapeutic purine-containing compounds

Scheme of C-H activation

 

Selected Publications

  • The elusive structure of Pd2(dba)3: Examination by isotopic labeling, NMR spectroscopy and X-ray diffraction analysis: synthesis and characterization of Pd2(dba-Z)3 complexes
    A R Kapdi, A C Whitwood, D C Williamson, J M Lynam, M J Burns, T J Williams, A J Reay, J Holmes, and I J S Fairlamb, J. Am. Chem. Soc. 2013, 135, 8388-8399.
  • A remarkable cis- and trans-spanning dibenzylidene acetone diphosphine chelating ligand (dbaphos)
    A G Jarvis, P E Sehnal, S E Bajwa, A C Whitwood, X Zhang, M S Cheung, Z Lin, and I J S Fairlamb, Chem. Eur. J. 2013, 19, 6034-6043.
  • Evidence for the Surface Catalysed Suzuki-Miyaura Reaction over Pd Nanoparticles: an Operando XAS Study
    P J Ellis, I J S Fairlamb S F J Hackett, K Wilson and A F Lee, Angew Chem Int Ed 2010, 49, 1820-1824.
  • Remarkable anion effects uncovered in the development of a Au(III)-catalyzed tandem nucleophillic substitution-1,5-enyne cycloisomerization process
    J P Reeds, A C Whitwood, M P Healy, I J S Fairlamb, Chem Commun 2010, 46, 2046–2048.
  • Ion-tagged π-acidic alkene ligands promote Pd-catalysed allyl-aryl couplings in an ionic liquid
    P S Bäuerlein, I J S Fairlamb, A G Jarvis, A F Lee, C Müller, J M Slattery, R J Thatcher, D Vogt and A C Whitwood, Chem Commun, 2009, 5734-5736.
  • Pd(0)/Cu(I)-Mediated direct arylation of 2'-deoxyadenosines: mechanistic role of Cu(I) and reactivity comparisons with related purine nucleosides
    T E Storr, C G Baumann, R J Thatcher, S De Ornellas, A C Whitwood and I J S Fairlamb, J Org Chem, 2009, 74, 5810-5821.
  • Site-selective direct arylation of unprotected adenine nucleosides mediated by palladium and copper: insights into the reaction mechanism.
    T E Storr, A G Firth, K Wilson, K Darley, C G Baumann and I J S Fairlamb, Tetrahedron, 2008, 64, 6125-6137.
  • In-silico prediction of Pd-catalysed cross-coupling processes: dibenzylidene acetone (dba) ligand control.
    I J S Fairlamb and A F Lee, Organometallics, 2007, 26, 4087-4089.
  • 2-Alkyne dicobalt(0)hexacarbonyl complexes as carbon monoxide-releasing molecules (CO-RMs): probing the release mechanism
    A J Atkin, S Williams, P Sawle, R Motterlini, J M Lynam and I J S Fairlamb, Dalton Trans, 2009, 3653–3656.
  • η1 -2-Pyrone metal carbonyl complexes as CO-releasing molecules (CO-RMs): A delicate balance between stability and CO liberation.
    I J S Fairlamb, J M Lynam, B E Moulton, I E Taylor, A K Duhme-Klair, P Sawle and R Motterlini, Dalton Trans, 2007, 3603-3609.

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York Research Database link

Research

Overview

We are an Organic Chemistry research group with strong multi-disciplinary links to Inorganic Chemistry, Chemical Biology and Nanoscience.

Current projects

Catalytic C-H Activation in biomolecules.

Organometallic CO-releasing therapeutics.

Alkene ligands for Pd catalysis.

Pseudohalide ligands for metal catalysis.

 

 

Research group(s)

The research group is made up of PhD students, post-doctoral scientists, M.Chem. students and research visitors.

Collaborators

Current York collaborators:

Current External collaborators:

Available PhD research projects

Please contact Prof. Fairlamb about new research projects available within the group.