Publications

Use the table of contents below to navigate to publications by year or by theme. You can also check out Dave's publications on his Google Scholar page.

Publications by year

Independent work

Mentored work

Publications by theme

Synthesis of iodonium and sulfonium arylation reagents

Arylation reactions via ligand coupling from iodine(III)

Arylation reactions via aryne intermediates

Bonding, structure and mechanisms

Primers, book chapters, reviews, and perspectives

Mentored work

Publications by year

Independent work

44. Hatton, J.; Jha, S.; Bonagiri, N.; Stuart, D. R. One-pot Synthesis of Aryl(TMP)iodonium Triflate Salts. J. Org. Chem. 2025, 90, 12001-12006.

43. Metze, B. E.; Farris, C.; Hatton, J.; Stuart, D. R. Rapid Access to Arynes from Aryl Triflates Using a Non-competitive, Commercially Available Amide Base. Tetrahedron, 2025, DOI: 10.1016/j.tet.2025.134856

42. Jha, S.; Basu, S.; Bob, M.; Stuart, D. R. The Lewis basicity of amines on the Legault iodonium Lewis acidity scale. Chem. Commun. 2025, 61, 11842.

41. Stuart, D. R. Synthesis of aryl(TMP)iodonium salts and their arylation reactions. Synlett 2025, 36, 1669-1678 (invited account).

40. Roberts, R. A.; Metze, B. E.; Javaly, N.; McCormick, T. M.; Stuart, D. R. Access to Arynes from Arene via Net Dehydrogenation: Scope, Synthetic Applications, and Mechanistic Analysis. Chem. Sci. 2025, 16, 5547-5558.

39. Hatton, J.; Stuart, D. R. Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C-N Coupling. Org. Lett., 2025, 27, 1130-1135.

38. Stuart, D. R. Diaryliodonium Salts. ACS In Focus (primer), 2024, DOI: 10.1021/acsinfocus.7e8008.

37. Roberts, R.; Stuart, D. R. Aryl Thianthenium Triflates. eEROS, 2024, DOI: 10.1002/047084289X.rn02567

36. Javaly, N.; McCormick, T. M.; Stuart, D. R. A Comparison of Structure, Bonding, and Non-covalent Interactions of Aryl Halide and Diaryliodonium Halogen-Bond Donors. Beilstein J. Org. Chem. 2024, 20, 1428-1435.

35. Gallagher, R. T.; Jha, S.; Metze, B. E.; Stuart, D. R. Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism. Synlett, 2024, 35, 889-894.

34. Metze, B. E.; Roberts, R. A.; Nilova, A.; Stuart, D. R. An Efficient and Chemoselective Method to Generate Arynes. Chem. Sci., 2023, 14, 13885-13892.

33. Karandikar, S. S.; Metze, B. E.; Roberts, R. A. Stuart, D. R. Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence. Org. Lett., 2023, 25, 6374-6379.

32. Roberts, R. A.; Metze, B. E.; Nilova, A.; Stuart, D. R. Synthesis of Arynes via Formal Dehydrogenation of Arenes. J. Am. Chem. Soc., 2023, 145, 3306-3311.

31. Metze, B. E.; Bhattacharjee, A.; McCormick, T. M.; Stuart, D. R. Parameterization of Arynophiles: Experimental Investigations towards a Quantitative Understanding of Aryne Trapping Reactions. Synthesis, 2022, 54, 4989-4996.

30. Karandikar, S. S.; Stuart, D. R. Refining Boron-Iodane Exchange to Access Versatile Arylation Reagents. Chem. Commun. 2022, 58, 1211-1214.

29. Karandikar, S. S.; Bhattacharjee, A.; Metze, B. E.; Javaly, N.; Valente, E. J.; McCormick, T. M.; Stuart, D. R. Orbital Analysis of Bonding in Diarylhalonium Salts and Relevance to Periodic Trends in Structure and Reactivity. Chem. Sci. 2022, 13, 6532-6540.

28. Pou, S.; Dodean, R. A.; Frueh, L.; Liebman, K. M.; Gallagher, R. T.; Jin, H.; Jacobs, R. T.; Nilsen, A.; Stuart, D. R.; Doggett, J. S.; Riscoe, M. K.; Winter, R. W. A New Scalable Synthesis of ELQ-300, ELQ-316, and other Antiparasitic Quinolones. Org. Process Res. Dev., 2021, 25, 1841-1852.

27. Nilova, A.; Metze, B. E.; Stuart, D. R. Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes. Org. Lett. 2021, 23, 4813-4817.

26. Nilova, A.; Sibbald, P. A.; Valente, E. J.; Gonzalez-Montiel, G. A.; Richardson, H. C.; Brown, K. S.; Cheong, P. H.-Y.; Stuart, D. R. Regioselective Synthesis of 1,2,3,4-Tetrasubstituted Arenes by Vicinal Functionalization of Arynes Derived from Aryl(Mes)iodonium Salts. Chem. Eur. J. 2021, 27, 7168-7175.

25. Nilova, A.; Campeau, L.-C.; Sherer, E. C.; Stuart, D. R. Analysis of Benzenoid Substitution Patterns in Small Molecule Active Pharmaceutical Ingredients. J. Med. Chem. 2020, 63, 13389-13396.

24. Gallagher, R. T.; Basu, S.; Stuart, D. R. Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers. Adv. Synth. Catal., 2020, 362, 320-325.

23. Gallagher, R. T.; Seidl, T. L.; Bader, J.; Orella, C.; Vickery, T.; Stuart, D. R. Anion Metathesis of Diaryliodonium Tosylate Salts with a Solid-phase Column Constructed from Readily Available Laboratory Consumables. Org. Process Res. Dev., 2019, 23, 1269-1274.

22. Seidl, T. L.; Moment, A.; Orella, C.; Vickery, T.; Stuart, D. R. Synthesis of 4-Methylbenzoate(2',4',6'-trimethoxyphenyl)iodonium Tosylate. Org. Synth., 2019, 96, 137-149.

21. Basu, S.; Sandtorv, A. H.; Stuart, D. R. Imide Arylation with Aryl(TMP)iodonium Tosylates. Beilstein J. Org. Chem., 2018, 14, 1034-1038.

20. Stuart, D. R. Aryl Transfer Selectivity in Metal-Free Reactions of Unsymmetical Diaryliodonium Salts. Chem. Eur. J., 2017, 23, 15852-15863.

19. Seidl, T. L.; Stuart, D. R. An Admix Approach to Determine Counter Anion Effects in Metal-Free Arylation Reactions with Diaryliodonium Salts. J. Org. Chem., 2017, 82, 11765-11771.

18. Carreras, V.; Sandtorv, A. H.; Stuart, D. R. Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetates Salts. J. Org. Chem., 2017, 82, 1279-1284.

17. Stuart, D. R. Unsymmetrical Diaryliodonium Salts as Aryne Synthons: Renaisance of a C-H Deprotonative Approach to Arynes. Synlett, 2017, 28, 275-279.

16. Sandtorv, A. H.; Stuart, D. R. Metal-Free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution. Angew. Chem. Int. Ed., 2016, 55, 15812-15815.

15. Sundalam, S. K.; Seidl, T. L.; Nilova, A.; Stuart, D. R. A Selective C-H Deprotonation Strategy to Access Functionalized Arynes by Using Hypervalent Iodine. Angew. Chem. Int. Ed., 2016, 55, 8431-8434.

14. Seidl, T. L.; Sundalam, S. K.; McCullough, B.; Stuart, D. R. Unsymmetrical Aryl(2,4,6-trimethoxyphenyl)iodonium Salts: One-pot Synthesis, Scope, Stability, and Synthetic Studies. J. Org. Chem., 2016, 81, 1998-2009.

13. Sundalam, S. K.; Stuart, D. R. Base Mediated Synthesis of Alkyl Aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetrical Diaryliodonium Salts. J. Org. Chem., 2015, 80, 6456-6466.

12. Stuart, D. R.; Fagnou, K. The Discovery and Development of a Palladium(II)-Catalyzed Cross-Coupling of Two Unactivated Arenes. Top. Organomet. Chem. (Inventing Reactions), 2013, 44, 91-120.

Mentored work

11. Zou, J.; Berg, D. J.*; Stuart, D. R.; McDonald, R.; Twamley, B. Carbazole-bis(oxazolines) as Monoanionic, Tridentate Chelates in Lanthanide Chemistry: Synthesis and Structural Studies of Thermally Robust and Kinetically Stable Dialkyl and Dichloride Complexes. Organometallics, 2011, 30, 4958-4967.

10. Heustis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic Substituted Indoles and Pyrroles. Angew. Chem. Int. Ed., 2011, 50, 1338-1341.

9. Stuart, D. R.*; Alsabeh, P.; Kuhn, M.; Fagnou, K. Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles. J. Am. Chem. Soc., 2010, 132, 18326-18339.

8. Sun, H.Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.*; Fagnou, K. Mechanistic Analysis of Azine N-Oxide Direct Arylation: Evidence for a Critical Role of Acetate in the Pd(OAc)2 Precatalyst. J. Org. Chem., 2010, 75, 8180-8189.

7. Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H.-Y.; Guimond, N.; Lasserre, S.; Lecavallier, M.; Fagnou, K. Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope, and Application in Synthesis. J. Am. Chem. Soc., 2009, 131, 3291-3306.

6. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. Indole Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling of Acetanilides and Internal Alkynes. J. Am. Chem. Soc., 2008, 130, 16474-16475.

5. Liegault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K.* Intramolecular Pd(II)-Catalyzed Oxidative Biaryl Synthesis Under Air: Reaction Development and Scope. J. Org. Chem., 2008, 73, 5022-5028.

4. Stuart, D. R.; Villemure, E.; Fagnou, K. Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling. J. Am. Chem. Soc., 2007, 129, 12072-12073.

3. Stuart, D. R.; Fagnou, K. The Catalytic Cross-Coupling of Unactivated Arenes. Science, 2007, 316, 1172-1175.

2. Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Recent Advances in Intermolecular Direct Arylation Reactions. Aldrichemica Acta, 2007, 40, 35-41.

1. Aliaga, C.; Stuart, D. R.; Aspee, A.; Scaiano, J. C. Solvent Effects on Hydrogen Abstraction Reactions from Lactones with Antioxidant Properties. Org. Lett., 2005, 7, 3665 – 3668.

Publications by theme

Synthesis of iodonium and sulfonium arylation reagents

Arylation reactions via ligand coupling from iodine(III)

Arylation reactions via aryne intermediates

Bonding, structure and mechanisms

Primers, book chapters, reviews, and perspectives

Stuart, D. R. Synthesis of aryl(TMP)iodonium salts and their arylation reactions. Synlett 2025, 36, 1669-1678 (invited account).
Stuart, D. R. Diaryliodonium Salts. ACS In Focus (primer), 2024, DOI: 10.1021/acsinfocus.7e8008.
Roberts, R.; Stuart, D. R. Aryl Thianthenium Triflates. eEROS, 2024, DOI: 10.1002/047084289X.rn02567
Nilova, A.; Campeau, L.-C.; Sherer, E. C.; Stuart, D. R. Analysis of Benzenoid Substitution Patterns in Small Molecule Active Pharmaceutical Ingredients. J. Med. Chem. 2020, 63, 13389-13396.
Stuart, D. R. Aryl Transfer Selectivity in Metal-Free Reactions of Unsymmetical Diaryliodonium Salts. Chem. Eur. J., 2017, 23, 15852-15863.
Stuart, D. R. Unsymmetrical Diaryliodonium Salts as Aryne Synthons: Renaisance of a C-H Deprotonative Approach to Arynes. Synlett, 2017, 28, 275-279.
Stuart, D. R.; Fagnou, K. The Discovery and Development of a Palladium(II)-Catalyzed Cross-Coupling of Two Unactivated Arenes. Top. Organomet. Chem. (Inventing Reactions), 2013, 44, 91-120.

Mentored work

Zou, J.; Berg, D. J.*; Stuart, D. R.; McDonald, R.; Twamley, B. Carbazole-bis(oxazolines) as Monoanionic, Tridentate Chelates in Lanthanide Chemistry: Synthesis and Structural Studies of Thermally Robust and Kinetically Stable Dialkyl and Dichloride Complexes. Organometallics, 2011, 30, 4958-4967.
Heustis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic Substituted Indoles and Pyrroles. Angew. Chem. Int. Ed., 2011, 50, 1338-1341.
Stuart, D. R.*; Alsabeh, P.; Kuhn, M.; Fagnou, K. Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles. J. Am. Chem. Soc., 2010, 132, 18326-18339.
Sun, H.Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.*; Fagnou, K. Mechanistic Analysis of Azine N-Oxide Direct Arylation: Evidence for a Critical Role of Acetate in the Pd(OAc)2 Precatalyst. J. Org. Chem., 2010, 75, 8180-8189.
Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H.-Y.; Guimond, N.; Lasserre, S.; Lecavallier, M.; Fagnou, K. Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope, and Application in Synthesis. J. Am. Chem. Soc., 2009, 131, 3291-3306.
Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. Indole Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling of Acetanilides and Internal Alkynes. J. Am. Chem. Soc., 2008, 130, 16474-16475.
Liegault, B.; Lee, D.; Huestis, M. P.; Stuart, D. R.; Fagnou, K.* Intramolecular Pd(II)-Catalyzed Oxidative Biaryl Synthesis Under Air: Reaction Development and Scope. J. Org. Chem., 2008, 73, 5022-5028.
Stuart, D. R.; Villemure, E.; Fagnou, K. Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling. J. Am. Chem. Soc., 2007, 129, 12072-12073.
Stuart, D. R.; Fagnou, K. The Catalytic Cross-Coupling of Unactivated Arenes. Science, 2007, 316, 1172-1175.
Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Recent Advances in Intermolecular Direct Arylation Reactions. Aldrichemica Acta, 2007, 40, 35-41.
Aliaga, C.; Stuart, D. R.; Aspee, A.; Scaiano, J. C. Solvent Effects on Hydrogen Abstraction Reactions from Lactones with Antioxidant Properties. Org. Lett., 2005, 7, 3665 – 3668.