The University of Sheffield
Department of Chemistry

Joe HarrityProf. Joseph P. A. Harrity

Professor of Synthetic Organic Chemistry

Room: C74

Tel: +44-(0)114-22-29496

Fax: +44-(0)114-22-29436

email:

 


 

General  Research Teaching

Biographical Sketch

Prof. Harrity obtained his BSc (Hons.) in Chemistry from the University of Strathclyde in 1991, followed by a PhD from the same institution in 1994. He was a  Postdoctoral Research Fellow at Boston College, USA from 1994 to 1997, after which he became a Lecturer at the University of Sheffield. Here he was promoted to Senior Lecturer and Reader. He was promoted to Professor in 2009. In October 2012, Prof. Harrity was appointed to a 3 year Royal Society Industry Fellowship to undertake a collaboration with Peakdale Molecular. He will work with Peakdale to develop novel functionalised intermediates on commercially relevant scales, thereby introducing new scaffolds into their catalogue portfolio.

Awards

Pfizer Discovery Award (2004); AstraZeneca Research Award (2006); Royal Society Industry Fellowship (2012-2015).

Research Keywords

Organometallic chemistry, carbon-carbon bond formation, asymmetric synthesis, catalysis, total synthesis.

Teaching Keywords

Organic Chemistry

Selected Publications:

  • A Mild Benzannulation through Directed Cycloaddition Reactions, James D. Kirkham, Roger J. Butlin and Joseph P. A. Harrity, Angew Chem Int Edit 2012, 51, 6402-6405.
  • Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A, Nicole C. Mancey, Nicolas Sandon, Anne-Laure Auvinet, Roger J. Butlin, Werngard Czechtizky and Joseph P. A. Harrity, Chem. Commun. 2011, 47, 9804-9806.
  • A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters, Anne-Laure Auvinet and Joseph P. A. Harrity, Angew Chem Int Edit 2011, 50, 2769-2772.
  • Palladium-Catalyzed 1,3 -O-to-C Rearrangement of Pyrans toward Functionalized Cyclohexanones, Julien C. R. Brioche, Thomas A. Barker, David J. Whatrup, Michael D. Barker and Joseph P. A. Harrity, Org. Lett. 2010, 12, 4832-4835.
  • A borylative cyclisation towards indole boronic esters, J. H. Huang, S. J. F. Macdonald and J. P. A. Harrity, Chem. Commun. 2010, 46, 8770-8772.
  • Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters, A. L. Auvinet, J. P. A. Harrity and G. Hilt, J. Org. Chem. 2010, 75, 3893-3896.
  • Alkyne [3+2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles, D. L. Browne, J. B. Taylor, A. Plant and J. P. A. Harrity, J. Org. Chem. 2010, 75, 984-987.
  • Ambient Temperature Nitrogen-Directed Difluoroalkynylborane Carboni-Lindsey Cycloaddition Reactions, J. F. Vivat, H. Adams and J. P. A. Harrity, Org. Lett. 2010, 12, 160-163.
  • Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones, D. L. Browne, J. F. Vivat, A. Plant, E. Gomez-Bengoa and J. P. A. Harrity, J. Am. Chem. Soc. 2009, 131, 7762-7769.
  • Cross Coupling of Bromo Sydnones: Development of a Flexible Route toward Functionalized Pyrazoles, D. L. Browne, J. B. Taylor, A. Plant and J. P. A. Harrity, J. Org. Chem. 2009, 74, 396-400. 

 

Research InterestsResearch Harrity 1

Synthesis provides the opportunity to design and prepare specific molecules whilst exploring novel processes that further develop the field of organic chemistry. In this context, our programme has concentrated on new and selective carbon-carbon bond forming strategies for the preparation of functionalised synthetic Intermediates. A summary of projects currently under investigation is outlined below:

Alkynylboronate Cycloadditions. Aromatic boronic acids and esters are extremely useful and versatile substrates in modern organic chemistry. We have developed a strategically novel approach to these compounds through cycloaddition reactions of alkynylboronates. To date, this approach has allowed us to generate boronic esters that are connected to benzene, quinone, pyridine, pyrazole, isoxazole and pyridazine scaffolds.

[3 + 3] Annelation Reactions. We have designed an efficient method for the synthesis of piperidines and pyrans by the addition of conjunctive reagents to aziridines and epoxides. Moreover, the ready availability of enantiopure aziridnes/epoxides has allowed to us to employ this technique in the stereoselective synthesis of alkaloid natural products, as well as bioactive compounds of marine origin.Research Harrity 2

Organocobalt complexes. A Lewis acid catalysed rearrangement reaction of cobalt-alkyne complexes bearing a cyclic enol ether unit has been developed that provides a direct and stereoselective route to 3-alkynylcycloalkanones. A catalytic variant of this process is currently under investigation as is its employment in target synthesis.

Teaching Section

Organic Chemistry

Undergraduate Courses Taught

  • Introduction to organic synthesis 2 (Year 2)
    This segment will discuss the α-functionalisation of carbonyl derivatives and related compounds. Specifically, alkylation and acylation reactions will be introduced and their applications in synthesis described. Simple examples highlighting chemoselective oxidation and reduction processes will also be discussed.
  • Strategy in Synthesis 2 (Year 3)
    The course is designed to reinforce the ideas of retrosynthetic analysis introduced in Strategy in Synthesis 1, providing a basis for the design of synthetic routes to more complex molecules.
  • Stereoselective Synthesis (Year 4)
    This segment gives a broad overview on current methods for controlling stereochemistry in organic synthesis. Key concepts in controlling relative and absolute stereochemistry will be introduced and illustrated.

Tutorial & Workshop Support

  • Second Year Organic Chemistry Tutorials.
  • Third Year Workshops.
  • Fourth Year Workshops.
  • Third Year Literature Review.

Laboratory Teaching

  • Fourth Year Research Project.