Publications

Book Chapters

2. Graham K. Murphy* and Tanja Gulder,* "Hypervalent iodine fluorination for preparing alkyl fluorides (stoichiometrically and catalytically" in "Synthetic Organofluorine Chemistry: Fluorination" Springer, 2018.

1. Graham K. Murphy and F.G. West, "Oxonium Ylide Rearrangements in Synthesis" in Molecular Rearrangements in Organic Synthesis, Wiley, Oct. 2015. (Angewandte Review)

Journal Articles

50. Radell Echemendía, Carlee A. Montgomery, Fabio Cuzzucoli, Antonio C. B. Burtoloso* and Graham K. Murphy* "Direct Trifluoroethylation of Carbonyl Sulfoxonium Ylides Using Hypervalent Iodine Compounds" Beilstein Journal of Organic Chemistry, 2024, 20, 3182-3190.

BJOC TOC Image

49. Yulia A. Vlasenko,# Avery J. To,# Tess Fortier, Natasha M. Evans, Cole J. Lindsay, Peter J. Palermo, Thorsten Dieckmann and Graham K. Murphy*, "Synthesis and Application of D- and 13C-Labelled tert-Butyl Hoechst Dye", Journal of Labelled Compounds and Radiopharmaceuticals , 2024, accepted.

JLCR TOC Image

48. Natasha M. Evans, Lindsey R. Shivers, Avery J. To, Graham K. Murphy, and Thorsten Dieckmann, "Biophysical Characterization and Design of a Minimal Version of the Hoechst RNA Aptamer" Biochemical and Biophysical Research Communications, 2024, accepted. DOI: 10.1016/j.bbrc.2024.149908.

TOC graphic from paper

47. Radell Echemendía, Avery J. To, Graham K. Murphy,* and Antonio C. B. Burtoloso* "Copper-Catalyzed α-Arylation of Sulfoxonium Ylides using Hypervalent Iodine Compounds", Advanced Synthesis & Catalysis, 2023, 366 (3), 396-401.

Radell AS&C TOC Graphic

46. Carlee A. Montgomery and Graham K. Murphy,* "Exploring the Role of Halogen Bonding in Iodonium Ylides: Insights into Unexpected Reactivity and Reaction Control" Beilstein J. Org. Chem., 202319, 1171–1190.

Carlee TOC

45. Léanne Racicot, John F. Valliant and Graham K. Murphy,* "Synthesis and Evaluation of Fluorous- and Polystyrene-Supported Precursors for Fluoro-benziodoxole" Synthesis, 2023, DOI: 10.1055/a-2085-3284

Synthesis 2023 TOC

44. Michael V. Tarasca, Cassidy J. Tomlinson, Dr. Pavel Gris and Dr. Graham K. Murphy,* "One-Step, Gram-Scale Synthesis of Caffeine-d9 from Xanthine and CD3I" Synthesis, 2022, 55(05) 821-825. (2023 Synform News Article)

Caffeine TOC Graphic

43. Carlee A. Montgomery,t Islam Jameel,t Fabio Cuzzucoli, Tristan Chidley, Dr. W. Scott Hopkins* and Dr. Graham K. Murphy,* Sigma-Holes in Iodonium Ylides: Halogen-Bond Activation of Carboxylic Acids, Phenols and Thiophenols May Enable Their X–H Insertion Reactions” Chem. Eur. J., 2022, 28(71), e202202029.

TOC Graphic

42. Fabio Cuzzucoli, Leanne Racicot, John F. Valliant and Graham K. Murphy,* “Transition metal-free fluorocyclization of unsaturated N-methoxyamides gives cyclic N-methoxyimidates” Tetrahedron, 2022, 123, 132982.

fluorocyclization

41. Avery J. To and Graham K. Murphy,* Iodolium Salts as Halogen-Bond Donor Catalysts in the Nazarov Cyclization: The Molecular Oxygen Enigma” New. J. Chem., 2022, 46, 15313 - 15320.

Nazarov TOC Graphic

40. Liam H. Britt, Zhensheng Zhao and Graham K. Murphy,* “Hypervalent Iodine-Mediated Oxidative Alkene Arylation: A Thorough Analysis” Can. J. Chem. 2022, 100(8), 606-621. (Keith Fagnou Award Lecture Paper)

Can J Chem TOC Graphic

39. Raed Al-Zoubi,* Walid K. Al-Jammal, Michael J. Ferguson and Graham K. Murphy, "Domino C–C/C–O bond formation: palladium-catalyzed regioselective synthesis of 7-iodobenzo[b]furans using 1,2,3-triiodobenzenes and benzylketones" RSC Advances, 2021, 11, 30069.

TOC Graphic

38. Zhensheng Zhao, Avery J. To and Dr. Graham K. Murphy*, "Difluorinative Ring Expansions of Benzo-Fused Carbocycles and Heterocycles are Achieved with p-(Difluoroiodo)toluene" Chem. Commun. 2019, 55, 14821.

ChemComm

37. Tristan Chidley, Islam Jameel, Shafa Rizwan, Philippe A. Peixoto, Dr. Laurent Pouységu, Dr. Stéphane Quideau,* Dr. W. Scott Hopkins* and Dr. Graham K. Murphy*, "Blue LED Irradiation of Iodonium Ylides Gives Diradical Intermediates for Efficient Metal-ˇfree Cyclopropanation with Alkenes" Angew. Chem. Int. Ed., 2019, 58, 16959. (Cover Art)

ACIE

36. Zhensheng Zhao, Kevin C.Y. Ma, Dr. Claude Y. Legault* and Dr. Graham K. Murphy*, "Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes" Chem. Eur. J., 2019, 25, 11240.

CF3 PAPER

35. Zhensheng Zhao, Islam Jameel and Graham K. Murphy*, "Vicinal Dichlorination of o-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl)fluorenes via Tandem Friedel-Crafts Alkylations" Synthesis, 2019, 51, 2648.

Synthesis FA TOC

34. Jason Tao and Graham K. Murphy*, "A Practical, Large-Scale Synthesis of p-(Difluoroiodo)toluene (p-TolIF2)" Synthesis, 2019, 51, 3055.

Synthesis PSP TOC

33. Tristan Chidley and Graham K. Murphy*, Cyclopropanation of Alkenes with Metallocarbenes Generated from Monocarbonyl Iodonium Ylides" Org. Biomol. Chem., 2018, 16, 8486.  (Invited submission to Theme Issue on Carbenes in Organic Synthesis)

TOC Graphic

32. 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 (64), 17002. (Synfacts highlight in 2019)

TOC

31. Jasmin Eljo and Graham K. Murphy*, "Direct, Oxidative Halogenation of Diaryl- or Dialkylphosphine oxides with (Dihaloiodo)arenes" Tetrahedron Lett., 2018, 59, 2965.

TOC

30. 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 issue on Hypervalent Iodine Chemistry)

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29. 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.

AJOC TOC

28. Zhensheng Zhao, Léanne Racicot and Graham K. Murphy* "Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of a-(Difluoromethyl)styrenes", Angew. Chem., Int. Ed., 2017, 56, 11620.

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27. Benjamin A. Laevens, Jason Tao and Graham K. Murphy*, " Iodide-Mediated Synthesis of Spirooxindolo Dihydrofurans from Iodonium Ylides and 3-Alkylidene-2-oxindoles" J. Org. Chem., 2017, 82, 11903. Invited submission to issue on Hypervalent Iodine Chemistry.

BL JOC TOC

26. Jason Tao, Carl D. Estrada and Graham K. Murphy*, " Metal-Free Intermolecular Cyclopropanation Between Alkenes and Iodonium Ylides Mediated By PhI(OAc)2• Bu4NI" Chem. Commum. 2017, 53, 9004.

Publication 25

25. Jasmin Eljo, Myriam S. Carle, and Graham K. Murphy*, " Hypervalent Iodine-Based Activation of Triphenylphosphine for the Functionalization of Alcohols" Synlett, 2017, 28, 2871. Invited submission to issue dedicated to Dr. Vic. Snieckus.

Synlett TOC

24. Zhensheng Zhao, Kaivalya G. Kulkarni, and Graham K. Murphy*, " Synthesis of Aryldihalomethanes by Denitrogenative Dihalogenation of Benzaldehyde Hydrazones" Adv. Synth. Catal. 2017, 359, 2222.

ASC TOC

23. Abhinandan Shyamsunder, Witali Beichel, Petra Klose, Quan Pang, Harald Scherer, Anke Hoffmann, Prof. Graham. K. Murphy, Prof. Ingo Krossing, Prof. Linda F. Nazar*, " Inhibiting polysulfide shuttle in Li-S batteries through low ion-pairing salts and a triflamide solvent" Angewandte Chem., Int. Ed., 2017, 56, 6192.

Publication 22

22. Kaivalya G. Kulkarni, Boris Miokovic, Matthew Sauder and Graham K. Murphy*, "Denitrogenative hydrofluorination of Aromatic Aldehyde Hydrazones Using (Difluoroiodo)toluene", Org. Biomol. Chem. 2016, 14, 9907-9911.

Publication 21

21. Geoffrey S. Sinclair, Richard Tran, Jason Tao, W. Scott Hopkins* and Graham K. Murphy*, “Borosilicate Activation of (Difluoroiodo)toluene in the gem-Difluorination of Phenyldiazoacetate Derivatives” Eur. J. Org. Chem. 2016, 27, 4603. (EurJOC Cover Art)

publication 20

20. Myriam S. Carle, Grace K. Shimokura and Graham K. Murphy*, ”Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic acids: In-Situ Synthesis of Ph3PCl2 Eur. J. Org. Chem. 2016, 23, 3930. (Top 10 downloaded article for August 2016.)

publication 19

19. Robert Black, Abhinandan Shyamsunder, Parvin Adeli, Dipan Kundu, Graham K. Murphy and Linda F. Nazar, "The Nature and Impact of Side Reactions in Glyme-based Sodium-Oxygen Batteries" ChemSusChem 2016, 9, 1-10.

publication 18

18. Jason Tao, Tina N. Tuck and Graham K. Murphy, "Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds via Double Ligand Transfer from (Dichloroiodo)benzene" Synthesis 2016, 48, 772–782.

publication 17

17. Charlotte Hepples and Graham K. Murphy, "Synthesis of 3,3-dichloro-2-oxindoles from isatin-3-p-tosylhydrazones and (dichloroiodo)benzene" Tet. Lett. 2015, 35, 4971.

Publication 16

16. Jason Tao and Graham K. Murphy, "(Difluoroiodo)toluene" e-EROS update May 2015.

15. Keith E. Coffey and Graham K. Murphy,"Dichlorination of α-Diazo-β-Dicarbonyls with (Dichloroiodo)benzene" Synlett 2015, 26, 1003. (Invited Synpacts Article)

Publication 14

14. Keith E. Coffey, Ryan Moreira, Farhana Z. Abbas and Graham K. Murphy, "Synthesis of 3,3-dichloroindolin-2-ones from Isatin-3-hydrazones and (Dichloroiodo)benzene" Org. Biomol. Chem. 2015, 3, 682.

Publication 13

13. Graham K. Murphy,* Farhana Z. Abbas and Amy V. Poulton, "a,a-Dichlorination of Oxindole Derivatives Using (Dichloroiodo)benzene," Adv. Synth. Cat. 2014, 356, 2919.

Publication 12

12. Brian D. Adams, Robert Black, Zack Williams, Russel Fernandes, Marine Cuisinier, Erik Jaemstorp Berg, Petr Novak, Graham K. Murphy, and Linda F. Nazar* "Towards a Stable Organic Electrolyte for the Lithium Oxygen Battery," Adv. Energy Mater2015, 5, 1400867.

11. Jason Tao, Richard Tran and Graham K. Murphy,* "Dihaloiodoarenes: a,a-Dihalogenation of Phenylacetate Derivatives," J. Am. Chem. Soc. 2013, 135 (44), pp 16312–16315. (Synfacts highlight in 2014)

Publication 10

10. 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.

Publication 9

9. Dr. Joyce C. Leung, Dr. Aaron A. Bedermann, Prof. Jón T. Njardarson, Prof. David A. Spiegel, Prof. Graham K. Murphy, Dr. Naoto Hama, Dr. Barry M. Twenter, Dr. Ping Dong, Prof. Tatsuya Shirahata, Dr. Ivar M. McDonald, Dr. Munenori Inoue, Dr. Nobuaki Taniguchi, Dr. Travis C. McMahon, Dr. Christopher M. Schneider, Dr. Nancy Tao, Prof. Brian M. Stoltz and Prof. John L. Wood,* "Total Synthesis of (±)-Phomoidride D", Angewandte. Chem., Int. Ed., 2018, 57, 1.

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8. 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.

Publication 8

7. 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, 477.

Publication 7

6. 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.

Publication 6

5. 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.

4. 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.

Publication 4

3. 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.

Publication 3

2. 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.

Publication 2

1. Yusuke Shibuya, Hiroshi Kusuoku, Graham K. Murphy, and Yoshinori Nishizawa, “Isolation and Structure Determination of New Macrocarpals from a Herbal Medecine, Eucalyptus Globulus Leaf,” Journal of Natural Medicines, 2001, 55 (1), 28–31.