RSS-Feed abonnieren
DOI: 10.1055/a-2564-5120
Synthesis of Aryl(TMP)iodonium Salts and Their Arylation Reactions
This work has been funded in part by Portland State University, the American Chemical Society, Petroleum Research Fund (ACS PRF, DNI 54405), and the National Science Foundation (NSF CHE 1856705, 2154500, and 2247802).

This work is dedicated to all the students who have worked diligently in the lab to obtain the results summarized in this Account, and to colleagues across the globe working to advance the chemistry of aryl(TMP)iodonium salts.
Abstract
Diaryliodonium salts continue to emerge as versatile arylation reagents. This is especially true for unsymmetrical aryl(TMP)iodonium salts (TMP = 2,4,6-trimethoxyphenyl) because they undergo highly selective aryl transfer across diverse mechanistic settings. This account outlines our motivation for exploring the chemistry of aryl(TMP)iodonium salts and our efforts to develop streamlined synthetic methods to access them and the novel arylation reactions that use them.
Publikationsverlauf
Eingereicht: 28. Februar 2025
Angenommen nach Revision: 21. März 2025
Accepted Manuscript online:
21. März 2025
Artikel online veröffentlicht:
05. Mai 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Merritt E, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 2 Olofsson B. Top. Curr. Chem. 2015; 373: 135
- 3 Meng H, Liu M.-S, Shu W. Chem. Sci. 2022; 13: 13690
- 4 Roberts R, Stuart D. In Encyclopedia of Reagents for Organic Synthesis . Wiley; Weinheim: 2024: 1
- 5 Stuart DR. Chem. Eur. J. 2017; 23: 15852
- 6 Graskemper JW, Wang B, Qin L, Neumann KD, DiMagno SG. Org. Lett. 2011; 13: 3158
- 7 Rotstein BH, Stephenson NA, Vasdev N, Liang SH. Nat. Commun. 2014; 5: 4365
- 8 Chen Y, Gu Y, Meng H, Shao Q, Xu Z, Bao W, Gu Y, Xue X.-S, Zhao Y. Angew. Chem. Int. Ed. 2022; 61: e202201240
- 9 Hickey DM. B, Leeson PD, Novelli R, Shah VP, Burpitt BE, Crawford LP, Davies BJ, Mitchell MB, Pancholi KD, Tuddenham D, Lewis NJ, O’Farrell C. J. Chem. Soc., Perkin Trans. 1 1988; 3103
- 10 Oh CH, Kim JS, Jung HH. J. Org. Chem. 1999; 64: 1338
- 11 Dohi T, Yamaoka N, Kita Y. Tetrahedron 2010; 66: 5775
- 12 Dohi T, Yamaoka N, Itani I, Kita Y. Aust. J. Chem. 2011; 64: 529
- 13 Chun J.-H, Pike VW. J. Org. Chem. 2012; 77: 1931
- 14 Chun J.-H, Pike VW. Org. Biomol. Chem. 2013; 11: 6300
- 15 Yamaoka N, Sumida K, Itani I, Kubo H, Ohnishi Y, Sekiguchi S, Dohi T, Kita Y. Chem. Eur. J. 2013; 19: 15004
- 16 Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B. Chem. Eur. J. 2013; 19: 10334
- 17 Bielawski M, Olofsson B. Chem. Commun. 2007; 2521
- 18 Bielawski M, Zhu M, Olofsson B. Adv. Synth. Catal. 2007; 349: 2610
- 19 Zhu M, Jalalian N, Olofsson B. Synlett 2008; 592
- 20 Seidl TL, Sundalam SK, McCullough B, Stuart DR. J. Org. Chem. 2016; 81: 1998
- 21 Seidl TL, Stuart DR. J. Org. Chem. 2017; 82: 11765
- 22 Gallagher RT, Seidl TL, Bader J, Orella C, Vickery T, Stuart DR. Org. Process Res. Dev. 2019; 23: 1269
- 23 Seidl T. Org. Synth. 2019; 96: 137
- 24 Carlson R, Carlson JE. Design and Optimization in Organic Synthesis . In Data Handling in Science and Technology, 2nd revised and enlarged ed. Elsevier; Amsterdam: 2005
- 25 Carreras V, Sandtorv AH, Stuart DR. J. Org. Chem. 2017; 82: 1279
- 26 Lubinkowski JJ, Gomez M, Calderon JL, McEwen WE. J. Org. Chem. 1978; 43: 2432
- 27 Jalalian N, Ishikawa EE, Silva LF. Jr, Olofsson B. Org. Lett. 2011; 13: 1552
- 28 Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
- 29 Oae S, Uchida Y. Acc. Chem. Res. 1991; 24: 202
- 30 Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165
- 31 McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348
- 32 Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 33 Shearer J, Castro JL, Lawson AD. G, MacCoss M, Taylor RD. J. Med. Chem. 2022; 65: 8699
- 34 Sandtorv AH, Stuart DR. Angew. Chem. Int. Ed. 2016; 55: 15812
- 35 Ochiai M, Suefuji T, Miyamoto K, Tada N, Goto S, Shiro M, Sakamoto S, Yamaguchi K. J. Am. Chem. Soc. 2003; 125: 769
- 36 Ochiai M, Suefuji T, Shiro M, Yamaguchi K. Heterocycles 2006; 67: 391
- 37 Purkait N, Kervefors G, Linde E, Olofsson B. Angew. Chem. Int. Ed. 2018; 57: 11427
- 38 Kervefors G, Kersting L, Olofsson B. Chem. Eur. J. 2021; 27: 5790
- 39 Basu S, Sandtorv AH, Stuart DR. Beilstein J. Org. Chem. 2018; 14: 1034
- 40 Phan TB, Mayr H. J. Phys. Org. Chem. 2006; 19: 706
- 41 Breugst M, Tokuyasu T, Mayr H. J. Org. Chem. 2010; 75: 5250
- 42 Lancer KM, Wiegand GH. J. Org. Chem. 1976; 41: 3360
- 43 Hatton J, Stuart DR. Org. Lett. 2025; 27: 1130
- 44 Beringer FM, Brierley A, Drexler M, Gindler EM, Lumpkin CC. J. Am. Chem. Soc. 1953; 75: 2708
- 45 Ghosh R, Lindstedt E, Jalalian N, Olofsson B. ChemistryOpen 2014; 3: 54
- 46 Ghosh R, Olofsson B. Org. Lett. 2014; 16: 1830
- 47 Chan L, McNally A, Toh QY, Mendoza A, Gaunt M. J. Chem. Sci. 2015; 6: 1277
- 48 Lindstedt E, Stridfeldt E, Olofsson B. Org. Lett. 2016; 18: 4234
- 49 Reitti M, Gurubrahamam R, Walther M, Lindstedt E, Olofsson B. Org. Lett. 2018; 20: 1785
- 50 Kervefors G, Pal KB, Tolnai GL, Mahanti M, Leffler H, Nilsson UJ, Olofsson B. Helv. Chim. Acta 2021; 104: e2000220
- 51 Kikushima K, Miyamoto N, Watanabe K, Koseki D, Kita Y, Dohi T. Org. Lett. 2022; 24: 1924
- 52 Elboray EE, Bae T, Kikushima K, Kita Y, Dohi T. Adv. Synth. Catal. 2023; 365: 2703
- 53 Kikushima K, Tsuda T, Miyamoto N, Kita Y, Dohi T. Chem. Commun. 2024; 60: 10552
- 54 Sundalam SK, Stuart DR. J. Org. Chem. 2015; 80: 6456
- 55 Gallagher RT, Basu S, Stuart DR. Adv. Synth. Catal. 2020; 362: 320
- 56 Pou S, Dodean RA, Frueh L, Liebman KM, Gallagher RT, Jin H, Jacobs RT, Nilsen A, Stuart DR, Doggett JS, Riscoe MK, Winter RW. Org. Process Res. Dev. 2021; 25: 1841
- 57 Gallagher RT, Jha S, Metze BE, Stuart DR. Synlett 2024; 35: 889
- 58 Akiyama T, Imasaki Y, Kawanisi M. Chem. Lett. 1974; 229
- 59 Sundalam SK, Nilova A, Seidl TL, Stuart DR. Angew. Chem. Int. Ed. 2016; 55: 8431
- 60 Nilova A, Sibbald PA, Valente EJ, González-Montiel GA, Richardson HC, Brown KS, Cheong PH, Stuart DR. Chem. Eur. J. 2021; 27: 7168
- 61 Karandikar SS, Metze BE, Roberts RA, Stuart DR. Org. Lett. 2023; 25: 6374
- 62 Roberts RA, Metze BE, Javaly N, McCormick TM, Stuart DR. Chem. Sci. 2025; 5547
- 63 Nilova A, Metze B, Stuart DR. Org. Lett. 2021; 23: 4813
- 64 Fine Nathel NF, Morrill LA, Mayr H, Garg NK. J. Am. Chem. Soc. 2016; 138: 10402
- 65 Metze BE, Bhattacharjee A, McCormick TM, Stuart DR. Synthesis 2022; 54: 4989
- 66 Lanzi M, Dherbassy Q, Wencel-Delord J. Angew. Chem. Int. Ed. 2021; 60: 14852
- 67 Lanzi M, Rogge T, Truong TS, Houk KN, Wencel-Delord J. J. Am. Chem. Soc. 2023; 145: 345
- 68 Liu M, Jiang H, Tang J, Ye Z, Zhang F, Wu Y. Org. Lett. 2023; 25: 2777
- 69 Smith O, Hindson MJ, Sreenithya A, Tataru V, Paton RS, Burton JW, Smith MD. Nat. Synth. 2023; 3: 58
- 70 Yuan H, Yin W, Hu J, Li Y. Nat. Commun. 2023; 14: 1841
- 71 Metze BE, Roberts RA, Nilova A, Stuart DR. Chem. Sci. 2023; 14: 13885