Professor Jonathan M Percy

I first became interested in studying chemistry seriously at Merchant Taylors' School, Crosby, under the guidance of Dr Philip Loftus. I pursued a BSc at Imperial College of Science and Technology (1979-1982) under the tuition of Professors A. G. M.  Barrett,  S. V. Ley and the late C. W. Rees (inter alia), graduating from there with First Class Honours and leaving London to study towards a PhD in Physical Organic Chemistry at the University Chemical Laboratory, Cambridge under the supervision of Professor A. J. Kirby FRS.

My work involved the synthesis of new systems which would demonstrate intramolecular catalysis of acetal hydrolysis. The synthetic work required new developments in directed aromatic metallation reactions¹ as we tried to make peri-disubstituted naphthalenes and other arenes which contained strong (and strain relieving) intramolecular O-H…N hydrogen bonds.

We observed the catalytic effect we sought² and discovered some other interesting consequences of molecular strain along the way.³

I pursued post-doctoral work in Cambridge, looking at correlations between bond length changes in the solid state and indicators of solution reactivity⁴, then gained a Temporary Lectureship at the University of Durham (1988).

I held a position there until Spring 1990, then moved into Industry for 4 months, working at ICI Fine Chemicals Manufacturing Organisation in Blackley, Manchester within the Physical Organic Group led by (then) Dr J. H. Atherton and Dr B. G. Cox.

I worked on a problem in benzodifuranone dyestuff synthesis, becoming aware of the often complex mechanistic problems which are raised by large scale synthesis of organic compounds.

In 1990, I secured a Lectureship at Keele University where I was able to pursue independent research into fluorinated organic molecules, an interest stimulated by Professor R. D. Chambers FRS during my time in Durham.

I spent two years at Keele, moving to the University of Birmingham in 1992 as one of the first appointees of Professor Sir J. F. Stoddart FRS as he restructured the School of Chemistry.

I was active in all aspects of the life of the School during nine years there, developing my distinctive research theme in the synthesis of selectively-fluorinated organic molecules. We developed difluorinated acyl anion equivalents from trifluoroethanol⁵, using them to synthesise difluorinated allylic alcohols which could be rearranged effectively to install a CF₂ group within highly-functionalised environments.⁶

We also developed new strategies for making chemical mimics of important phosphate esters from nature (phosphotyrosine mimetics⁷, components for nucleic acid analogues⁸, inositol phosphonates⁹).

We found new applications of new refrigerants HCFC-133a¹⁰ and HFC-134a¹¹ and began to develop powerful synthetic pericyclic reactions like the Diels-Alder cycloaddition¹² and neutral oxy-Cope rearrangement¹³ for the synthesis of selectively fluorinated molecules, and used catalytic asymmetric methods, combined with Pd-catalysed coupling reactions to prepare fluorinated analogues of carbohydrates in high enantiomeric purity.¹⁴

I received a Pfizer Science Award (1997) and visited Japan in 1998 (2 months, University of Okayama Fellowship) to lecture on this work

In 2001, I took a Research Chair in Chemistry at the University of Leicester where I pursued these interests and began to develop our interests in asymmetric chemistry and in analogues of monosaccharides and cyclitols more strongly.

We used RCM¹⁵, and Sharpless AD chemistry¹⁶ to prepare difluorinated aldonic acids in racemic and enantiomerically enriched forms respectively via short sequences.

We also developed highly telescoped routes to novel difluorinated analogues of cyclitols¹⁷ and novel bicyclic analogues of sugars and their phosphates¹⁸. I re-visited Japan in 2004 (One month JSPS Fellowship) to lecture on this research work.

In a very significant development, my interests in Physical Organic Chemistry were rekindled by a number of observations of extreme reactivity brought about by the presence of fluorine atoms in organic reactions, and we began to measure rate constants and require significant help from computational chemistry, which Professor I. H. Hillier (external link) (University of Manchester) was able to offer to us.

My most recent move took place in July 2006, bringing me to WestCHEM at the University of Strathclyde as WestCHEM Professor of Synthetic Chemistry. Please read on to find out about my most recent and current research interests and publications.

Jump to currently available postgraduate studentships.

Teaching Interests and Experience

I have been consistently committed to the delivery of research-led high quality undergraduate teaching of both synthetic and mechanistic chemistry. I have delivered courses in the following areas:

First year teaching

Functional Group-type courses (Birmingham, Leicester, Keele) covering alkanes, alkenes, alkynes, alkyl halides, chemistry of the carbonyl group, introduction to synthetic analysis and planning, stereochemistry (enantiomers and diastereoisomers, stereoselective and stereospecific reactions).

Courses from 10-20 lectures delivered to 30-200 students.

Second year teaching

Selective reactions (Keele, reduction/oxidation and reagent chemistry, aminoacids and peptide synthesis), Control and Selectivity in Synthesis (Birmingham, enamines, enolates, ketoesters and some main group chemistry especially boron reagents), alicyclic chemistry (Birmingham and Leicester, small to normal rings, conformation, strain and I-strain, intramolecularity, anomeric and related effects), organic reaction mechanisms (elimination, carbenes, Durham).

Courses from 10-20 lectures delivered to 30-80 students.

Third year teaching

Advanced synthetic methods (Keele and Birmingham, phosphorus-based reagents, polarity reversal, silicon reagents), Reactive intermediates (Durham and Birmingham, carbenium ions, arynes, carbenes and nitrenes, free radicals, diazo reagents in synthesis, Bergman cyclisations), Organometallic chemistry (Birmingham, mainly, Pd, Zr and Cu chemistries), Rearrangements in synthesis (Birmingham, [3,3]-Claisen, [2,3]-Wittig, oxy-Cope).

Courses from 10-20 lectures delivered to 30-70 students.

Year four and PG teaching

Organofluorine chemistry (Leicester, case studies in bioactive fluorinated compounds, synthetic methods), Synthetic methods (Leicester synoptic course for MSc, Pd chemistry, metathesis, radicals), Frontiers in Chemistry (Birmingham, colloquium-based workshop series).

Courses from 10-15 lectures delivered to up to 20 students.

Rearrangements in synthesis (Masters-level course, Okayama, Japan, [3,3]-Claisen, [2,3]-Wittig, oxy-Cope).

I have also devised and implemented new practical courses at all levels (Durham, Keele and Birmingham) and am a co-author of Experimental Organic Chemistry (external link), a leading textbook (Harwood, Moody and Percy, Blackwell) on practical chemistry.

In Strathclyde, I teach the 13.163 and 13.110 Foundation level courses in Organic chemistry and deliver half of 13.252 Organic Chemistry (second year course) which develops ideas about how mechanism and synthetic applications combine.

References in order

1. Kirby, A. J.; Percy, J. M. Tetrahedron 1988, 44, 6903.
2. Kirby, A. J.; Percy, J. M. J. Chem. Soc., Chem. Commun. 1987, 177; Kirby, A. J.; Percy, J. M. J. Chem. Soc., Perkin Trans.2 1989, 907.
3. Kirby, A. J.; Percy, J. M. Tetrahedron 1988, 44, 6911.
4. Amos, R. D.; Handy, N. C.; Jones, P. G.; Kirby, A. J.; Parker, J. K.; Percy, J. M.; Su, M. D. J. Chem. Soc., Perkin Trans.2 1992, 549.
5. Patel, S. T.; Percy, J. M.; Wilkes, R. D. Tetrahedron 1995, 51, 9201.Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289.
6. Patel, S. T.; Percy, J. M.; Wilkes, R. D. J. Org. Chem. 1996, 61, 166; Balnaves, A. S.; Gelbrich, T.; Hursthouse, M. B.; Light, M. E.; Palmer, M. J.; Percy, J. M. J. Chem. Soc., Perkin Trans.1 1999, 2525.
7. Cockerill, G. S.; Easterfield, H. J.; Percy, J. M.; Pintat, S. J. Chem. Soc., Perkin Trans.1 2000, 2591.
8. Butt, A. H.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2000, 1691.
9. Butt, A. H.; Kariuki, B. M.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2002, 682.
10. Bainbridge, J. M.; Brown, S. J.; Ewing, P. N.; Gibson, R. R.; Percy, J. M. J. Chem. Soc., Perkin Trans.1 1998, 2541.
11. Kanai, M.; Percy, J. M. Tetrahedron Lett. 2000, 41, 2453.
12. Crowley, P. J.; Fawcett, J.; Kariuki, B. M.; Moralee, A. C.; Percy, J. M.; Salafia, V. Org. Lett. 2002, 4, 4125; Crowley, P. J.; Fawcett, J.; Griffith, G. A.; Moralee, A. C.; Percy, J. M.; Salafia, V. Org. Biomol. Chem. 2005, 3, 3297.
13. Dimartino, G.; Gelbrich, T.; Hursthouse, M. B.; Light, M. E.; Percy, J. M.; Spencer, N. S. Chem. Commun. 1999, 2535.DiMartino, G.; Hursthouse, M. B.; Light, M. E.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Biomol. Chem. 2003, 1, 4423.
14. Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. Tetrahedron-Asymmetry 2005, 16, 347.
15. Audouard, C.; Fawcett, J.; Griffiths, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A. Org. Biomol. Chem. 2004, 2, 528.
16. Audouard, C.; Barsukov, I.; Fawcett, J.; Griffith, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A. Chem. Commun. 2004, 1526.
17. Audouard, C.; Fawcett, J.; Griffith, G. A.; Kérourédan, E.; Miah, A.; Percy, J. M.; Yang, H. L. Org. Lett. 2004, 6, 4269.
18. Miles, J. A. L.; Mitchell, L.; Percy, J. M.; Singh, K.; Uneyama, E. J. Org. Chem. 2007, 72, 1575.
19. Capon, B.; Guo, B. Z.; Kwok, F. C.; Siddhanta, A. K.; Zucco, C. Accounts Chem. Res. 1988, 21, 135; Capon, B.; Rycroft, D. S.; Watson, T. W.; Zucco, C. J. Am. Chem. Soc. 1981, 103, 1761.
20. Kresge, A. J. Chem. Soc. Rev. 1996, 25, 275; Chiang, Y.; Kresge, A. J. Science 1991, 253, 395; Kresge, A. J. Accounts Chem. Res. 1990, 23, 43.
21. Griffith, G. A.; Hillier, I. H.; Percy, J. M.; Roig, R.; Vincent, M. A. J. Org. Chem. 2006, 71, 8250.
22. Leroy, J.; Molines, H.; Wakselman, C. J. Org. Chem. 1987, 52, 290.
23. Mayr, H.; Kempf, B.; Ofial, A. R. Accounts Chem. Res. 2003, 36, 66; Mayr, H.; Ofial, A. R. Pure Appl. Chem. 2005, 77, 1807.
24. Griffith, G. A.; Hillier, I. H.; Moralee, A. C.; Percy, J. M.; Roig, R.; Vincent, M. A. J. Am. Chem. Soc. 2006, 128, 13130.
25. Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew. Chem.-Int. Edit. 2005, 44, 192.
26. Zhang, C. S.; Griffith, B. R.; Fu, Q.; Albermann, C.; Fu, X.; Lee, I. K.; Li, L. J.; Thorson, J. S. Science 2006, 313, 1291; Williams, G. J.; Zhang, C.; Thorson, J. S. Nature Chemical Biology 2007, 3, 657.