Research interests: synthetic organic chemistry; alternative approaches to metallocarbene and metallonitrene intermediates; organic electrolytes for lithium air batteries
Professor Graham Murphy’s area of expertise is synthetic organic chemistry, spanning both method development and target-oriented synthesis. The research in his group involves the development of synthetic reactions, and using his synthetic expertise to address issues of broader scientific concern, such as the design and synthesis of organic electrolytes for use in battery technologies.
Murphy received his B.Sc. (Chemistry, Co-op) from the University of Victoria. He then attended the University of Alberta for graduate school, where he held both the AHFMR and NSERC PGS-D awards. His postdoctoral appointments in natural product synthesis consisted of one year as a JSPS postdoctoral fellow at Tohoku University, Japan, and nearly three years as an NSERC postdoctoral fellow at Colorado State University. He then spent one year as a postdoctoral fellow with the Biorefining Conversions Network (BCN) at the University of Alberta. Murphy began his independent career at the University of Waterloo in 2011.
Postdoctoral, Biorefining Conversions Network, Department of Chemistry, University of Alberta; Department of Chemistry, Colorado State University; Department of Chemistry, Tohoku University
PhD, Organic Chemistry, University of Alberta, 2001
BSc, Chemistry, University of Victoria, 2006
Awards and Honours
|Year||Awards and Honours|
|2016||Early Researcher Award, Province of Ontario|
|2016||CNC-IUPAC Travel Award|
|2014||Tetrahedron Letters: Top 10 reviewer for 2014|
|2014||Outstanding Performance Award|
|2014||Thieme Chemistry Journal Award, Germany|
|2008-2010||NSERC Post-Doctoral Fellowship|
|2006-2007||Japan Society for the Promotion of Science (JSPS) Post-Doctoral Fellowship|
|2004||Novartis Pharmaceuticals Inc. Graduate Scholarship|
|2002-2007||Alberta Heritage Foundation for Medical Research Graduate Studentship (AHFMR)|
Halogenation of Organic Materials
Given the prevalence of fluorine in of pharmaceuticals (~20%), agrochemicals (~30%) and industrial chemicals (eg. Teflon®), new method of incorporating fluorine into organic scaffolds is of utmost importance. Professor Murphy has recently discovered a new approach to incorporating fluorine and chlorine into organic materials, using hypervalent iodine species as transfer agents. This chemistry holds broad appeal to a wide community, and is continuously being expanded to include structural scaffolds of industrial, medicinal and societal importance.
Organic Electrolyte Research
Although lithium-ion batteries are the state-of-the-art rechargeable power source for portable electronics, achieving the same level of efficacy in large-scale systems (eg. hybrid electric vehicles) requires fundamental innovation in materials. Professor Murphy’s experience in target-oriented synthesis and in fluorination methodologies is being applied to devising new, oxidatively stable organic electrolytes for use in large-scale rechargeable batteries.
Recent publications include:
- Tristan Chidley and Graham K. Murphy,* “Cyclopropanation of Alkenes with Metallocarbenes Generated from Monocarbonyl Iodonium Ylides” Org. Biomol. Chem. 2018, 16, 8486.
- Zhensheng Zhao, Liam H. Britt and Graham K. Murphy,* “Oxidative, Iodoarene-Catalyzed Intramolecular Alkene Arylation for the Synthesis of Polycyclic Aromatic Hydrocarbons” Chem. Eur. J., 2018, 24, 17002.
- Jasmin Eljo and Graham K. Murphy,* “Direct, Oxidative Halogenation of Diaryl- or Dialkylphosphine Oxides with (Dihaloiodo)arenes” Tetrahedron Lett., 2018, 59, 2965.
- Zhensheng Zhao and Graham K. Murphy,* "Chlorination of Phenylallene Derivatives with 1-Chloro-1,2- benziodoxol-3-one: Synthesis of vicinal-Dichlorides and Chlorodienes" Beilstein J. Org. Chem, 2018, 14, 796. (Invited submission to the Thematic Series on Hypervalent Iodine Chemistry in Organic Synthesis)
- Graham K. Murphy,* Léanne Racicot and Myriam S. Carle, " The Chemistry Between Hypervalent Iodine(III) Reagents and Organophosphorus Compounds", Asian J. Org. Chem. 2018, 7, 837.
Jason Tao, Richard Tran and Graham K. Murphy,* Dihaloiodoarenes: a,a-Dihalogenation of Phenylacetate Derivatives, J. Am. Chem. Soc.2013, 135 (44), 16312–16315.
Phyllis E. Ho, Jason Tao and Graham K. Murphy,* Wittig Reagents as Metallocarbene Precursors: In situ Generated Monocarbonyl Iodonium Ylides, Eur. J. Org. Chem., 2013, 6540.
Graham K. Murphy,* Craig Stewart and Frederick G. West,* “Intramolecular generation and rearrangement of oxonium ylides: methodology studies and their application in synthesis,” Tetrahedron,2013, 69, 2667.
Graham K. Murphy, Tatsuya Shirahata, Naoto Hama, Aaron Bedermann, Ping Dong, Travis C. McMahon, Barry M. Twenter, David A. Spiegel, Ivar M. McDonald, Nobuaki Taniguchi, Munenori Inoue, and John L. Wood,* “Towards the Synthesis of Phomoidride D,” J. Org. Chem. 2013, 78 (2), 477.
Graham K. Murphy, Naoto Hama, Aaron Bedermann, Ping Dong, Chris M. Schneider, Travis C. McMahon, Ran N. Tao, Barry M. Twenter, Davis A. Spiegel, John L. Wood, “Wharton Fragmentation-Based Approach to the Carbocyclic Core of the Phomoidrides,” Org. Lett.2012,14, 4544.
Graham K. Murphy, Frederik P. Marmsäter, F.G. West, “Polycyclic Oxonium Ylides: Use of Cyclic Acetals as Convenient Scaffolds in the Construction of Fused Bicyclic Compounds Containing a Medium Ring,”Can. J. Chem. 2006, 84, 1470–1486.
Graham K. Murphy, F.G. West, “[1,2]- or [2,3]-Rearrangement of Onium Ylides of Allyl and Benzyl Ethers and Sulfides via in Situ-Generated Iodonium Ylides,” Org. Lett. 2006, 8, 4359–4361.
Graham K. Murphy, F.G. West, “Hydrazulene Ring Systems via Heteroatom-Assisted [1,2]-Shift of Oxonium and Sulfonium Ylides,”Org. Lett. 2005, 7, 1801–1804.
Fredrik P. Marmsäter, Graham K. Murphy, F.G. West, “Cyclooctanoid Ring Systems from Mixed Acetals via Heteroatom-Assisted [1,2]-Shift of Oxonium Ylides,” J. Am. Chem. Soc. 2003, 125, 14724–14725.
Yusuke Shibuya, Hiroshi Kusuoku, Graham K. Murphy, and Yoshinori Nishizawa, “Isolation and Structure Determination of New Macrocarpals from a Herbal Medecine, Eucalyptus Globulus Leaf,”Natural Medicines, 2001, 55 (1), 28–31.
Kusuoku, Hiroshi; Shibuya, Yusuke; Ohashi, Sachihiro; Takagi, Yutaka; Okubo, Koji “Macrocarpals and ceramide formation promoters containing them” JP 2001055325, Feb 27, 2001.