Transition-Metal-Free N-Arylation of N-Methoxysulfonamides and N,O-Protected Hydroxylamines with Trimethoxyphenyliodonium (III) Acetates

Kotaro Kikushima; Aki Morita; Elghareeb E. Elboray; Taeho Bae; Naoki Miyamoto; Yasuyuki Kita; Toshifumi Dohi

doi:10.1055/a-1922-8846

Synthesis, Table of Contents

Synthesis 2022; 54(23): 5192-5202
DOI: 10.1055/a-1922-8846

feature

Transition-Metal-Free N-Arylation of N-Methoxysulfonamides and N,O-Protected Hydroxylamines with Trimethoxyphenyliodonium (III) Acetates

Kotaro Kikushima ∗

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

,

Aki Morita

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

,

Elghareeb E. Elboray

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

^bDepartment of Chemistry, Faculty of Science, South Valley University, Qena 83523, Egypt

,

Taeho Bae

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

,

Naoki Miyamoto

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

,

Yasuyuki Kita ∗

^cResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

,

Toshifumi Dohi ∗

^aCollege of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

^cResearch Organization of Science and Technology, Ritsumeikan University, 1-1-1, Nojihigashi, Kusatsu Shiga 525-8577, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

Trimethoxyphenyliodonium(III) acetate [TMP-iodonium(III) acetate] functions as an efficient arylation reagent for N,O-protected hydroxylamines, generating aniline derivatives in the absence of transition metal catalysts. Various N-methoxysulfonamides participated in the amination reaction to produce the corresponding N-methoxysulfonylanilines. This amination reaction was compatible with several protecting groups, including Troc (2,2,2-trichloroethoxycarbonyl), Cbz (benzyloxycarbonyl), Boc (tert-butoxycarbonyl), benzyl, acetyl, and silyl groups. This method uses TMP-iodonium(III) acetate and efficiently synthesizes various aniline derivatives that are versatile synthetic intermediates for functional organic molecules.

Key words

N-arylation - iodonium salt - sulfonamide - hydroxylamine - sulfa drug

Full Text

References

References

1a Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
1b Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564
1c Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
1d Dong X, Liu Q, Dong Y, Liu H. Chem. Eur. J. 2017; 23: 2481
1e Hendrick CE, Wang Q. J. Org. Chem. 2017; 82: 839
1f Murakami K, Perry GJ. P, Itami K. Org. Biomol. Chem. 2017; 15: 6071

2 Bunnett JF, Zahler RE. Chem. Rev. 1951; 49: 273

3a Pummer WJ, Wall LA. Science 1958; 127: 643
3b Godsell JA, Stacey M, Tatlow JC. Nature 1956; 178: 199
3c Brooke GM, Burdon J, Stacey M, Tatlow JC. J. Chem. Soc. 1960; 1768

4a Luo J, Zhang J. ACS Catal. 2016; 6: 873
4b Kikushima K, Koyama H, Kodama K, Dohi T. Molecules 2021; 26: 1365

5a Katritzky AR, Laurenzo KS. J. Org. Chem. 1988; 53: 3978
5b Pagoria PP, Mitchell AR, Schmidt RD. J. Org. Chem. 1996; 61: 2934
5c Mąkosza M, Białecki M. J. Org. Chem. 1998; 63: 4878
5d Błaziak K, Danikiewicz W, Mąkosza M. J. Am. Chem. Soc. 2016; 138: 7276
5e Mąkosza M. Synthesis 2017; 49: 3247

6 Tian Z.-Y, Ming X.-X, Teng H.-B, Hu Y.-T, Zhang C.-P. Chem. Eur. J. 2018; 24: 13744

7a Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2013; 135: 5000
7b Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2014; 136: 4496

For selected examples, see:

8a Dohi T, Maruyama A, Minamitsuji Y, Takenaga N, Kita Y. Chem. Commun. 2007; 1224
8b Moroda A, Togo H. Synthesis 2008; 1257
8c Dohi T, Takenaga N, Fukushima K, Uchiyama T, Kato D, Shiro M, Fujioka H, Kita Y. Chem. Commun. 2010; 46: 7697
8d Antonchick AP, Samanta R, Kulikov K, Lategahn J. Angew. Chem. Int. Ed. 2011; 50: 8605
8e Samanta R, Bauer JO, Strohmann C, Antonchick AP. Org. Lett. 2012; 14: 5518
8f Ito M, Kubo H, Itani I, Morimoto K, Dohi T, Kita Y. J. Am. Chem. Soc. 2013; 135: 14078
8g Lucchetti N, Scalone M, Fantasia S, Muñiz K. Adv. Synth. Catal. 2016; 358: 2093
8h Liang D, Yu W, Nguyen N, Deschamps JR, Imler GH, Li Y, MacKerell AD. Jr, Jiang C, Xue F. J. Org. Chem. 2017; 82: 3589
8i Dohi T, Sasa H, Dochi M, Yasui C, Kita Y. Synthesis 2019; 51: 1185
8j Sasa H, Mori K, Kikushima K, Kita Y, Dohi T. Chem. Pharm. Bull. 2022; 70: 106

For selected reviews, see:

9a Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
9b Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
9c Yusubov MS, Maskaev AV, Zhdankin VV. ARKIVOC 2011; (i): 370
9d Olofsson B. Top. Curr. Chem. 2016; 373. 135
9e Aradi K, Toth BL, Tolnai GL, Novák Z. Synlett 2016; 27: 1456
9f Villo P, Olofsson B. Arylations Promoted by Hypervalent Iodine Reagents. In Patai's Chemistry of Functional Groups (Hypervalent Halogen Compounds). Olofsson B, Marek I, Rappoport Z. Wiley; Chichester: 2019: 461-522
9g Takenaga N, Kumar R, Dohi T. Front. Chem. 2020; 8: 599026
9h Kikushima K, Elboray EE, Jiménez-Halla JO. C, Solorio-Alvarado CR, Dohi T. Org. Biomol. Chem. 2022; 22: 3231

10a Beringer FM, Drexler M, Gindler EM, Lumpkin CC. J. Am. Chem. Soc. 1953; 75: 2705
10b Beringer FM, Brierley A, Drexler M, Gindler EM, Lumpkin CC. J. Am. Chem. Soc. 1953; 75: 2708

11a Carroll MA, Wood RA. Tetrahedron 2007; 63. 11349
11b Linde E, Bulfield D, Kervefors G, Purkait N, Olofsson B. Chem 2022; 8: 850

12a Tinnis F, Stridfeldt E, Lundberg H, Adolfsson H, Olofsson B. Org. Lett. 2015; 17: 2688
12b Basu S, Sandtorv AH, Stuart DR. Beilstein J. Org. Chem. 2018; 14: 1034
12c Xu B, Han J, Wang L. Asian J. Org. Chem. 2018; 7: 1674
12d Kuriyama M, Hanazawa N, Abe Y, Katagiri K, Ono S, Yamamoto K. Chem. Sci. 2020; 11: 8295
12e Chen H, Wang L, Han J. Org. Lett. 2020; 22: 3581

13 Seidl TL, Stuart DR. J. Org. Chem. 2017; 82: 11765

14a Sandtorv AH, Stuart DR. Angew. Chem. Int. Ed. 2016; 55: 15812
14b Purkait N, Kervefors G, Linde E, Olofsson B. Angew. Chem. Int. Ed. 2018; 57: 11427
14c Bugaenko DI, Yurovskaya MA, Karchava AV. Org. Lett. 2018; 20: 6389

15 Yang Y, Wu X, Han J, Mao S, Qian X, Wang L. Eur. J. Org. Chem. 2014; 6854

16a Beletskaya IP, Davydov DV, Moreno-Mañas M. Tetrahedron Lett. 1998; 39: 5621
16b Zhou T, Chen Z.-C. Synth. Commun. 2002; 32: 903
16c Zhou T, Chen Z.-C. Heteroat. Chem. 2002; 13: 617
16d Niu H.-Y, Xia C, Qu G.-R, Zhang Q, Jiang Y, Mao R.-Z, Li D.-Y, Guo H.-M. Org. Biomol. Chem. 2011; 9: 5039
16e Lv T, Wang Z, You J, Lan J, Gao G. J. Org. Chem. 2013; 78: 5723
16f Howell TO, Huckaba AJ, Hollis TK. Org. Lett. 2014; 16: 2570
16g Koseki D, Aoto E, Shoji T, Watanabe K, In Y, Kita Y, Dohi T. Tetrahedron Lett. 2019; 60: 1281

17a Su X, Chen C, Wang Y, Chen J, Louac Z, Lic M. Chem. Commun. 2013; 49: 6752
17b Wang Y, Chen C, Peng J, Li M. Angew. Chem. Int. Ed. 2013; 52: 5323
17c Wang Y, Chen C, Zhang S, Lou Z, Su X, Wen L, Li M. Org. Lett. 2013; 15: 4794

18a Nilova A, Sibbald PA, Valente EJ, González-Montiel GA, Richardson HC, Brown KS, Cheongand PH.-Y, Stuart DR. Chem. Eur. J. 2021; 27: 7168
18b Nilova A, Metze B, Stuart DR. Org. Lett. 2021; 23: 4813

For the preparation of TMP-iodonium(III) salts, see:

19a Seidl TL, Sundalam SK, McCullough B, Stuart DR. J. Org. Chem. 2016; 81: 1998
19b Carreras V, Sandtorv AH, Stuart DR. J. Org. Chem. 2017; 82: 1279
19c Lindstedt E, Reitti M, Olofsson B. J. Org. Chem. 2017; 82: 11909
19d Dohi T, Koseki D, Sumida K, Okada K, Mizuno S, Kato A, Morimoto K, Kita Y. Adv. Synth. Catal. 2017; 359: 3503
19e China H, Koseki D, Samura K, Kikushima K, In Y, Dohi T. Data Brief 2019; 25: 104063

For selected examples, see:

20a -Ref. 12b
20b Ref. 13
20c Ref. 14a
20d Ref. 16g
20e Ref. 18b
20f Ref. 19d
20g Gallagher RT, Basu S, Stuart DR. Adv. Synth. Catal. 2020; 362: 320

21 Kikushima K, Miyamoto N, Watanabe K, Koseki D, Kita Y, Dohi T. Org. Lett. 2022; 24: 1924
22 Drews J. Science 2000; 287: 1960
23 The solvent effects are presumably attributed to the solubility of starting materials. The present N-arylation proceeds via ligand exchange of amide with acetate anion of TMP-iodonium acetate followed by ligand coupling. We assume that the low solubility of TMP-iodonium acetate in toluene increased the relative concentration of soluble amide, which might accelerate the rate of ligand exchange step.
24 When the reaction was conducted in toluene, 4-nitrophenyl acetate was generated as a side product via direct ligand coupling of 2i. In this case, addition of water to exclude potassium acetate suppressed the side reaction to afford 3ai in relatively high yield (84%).

25a Fukuyama T, Jow C.-K, Cheung M. Tetrahedron Lett. 1995; 36: 6373
25b Kan T, Fukuyama T. Chem. Commun. 2004; 353

For copper-catalyzed [1,3] methoxy rearrangement of N-methoxyamide, see:

26a Nakamura I, Jo T, Ishida Y, Tashiro H, Terada M. Org. Lett. 2017; 19: 3059
26b Ishida Y, Nakamura I, Terada M. J. Am. Chem. Soc. 2018; 140: 8629

27 For removal of methoxy group of N-methoxysulfonamide via pyrolysis, see: Li Q, Zhang M, Zhan S, Gu Z. Org. Lett. 2019; 21: 6374

28a Javorskis T, Orentas E. J. Org. Chem. 2017; 82: 13423
28b Newcomer R, McKee J, Zanger M. Synth. Commun. 2016; 46: 949

29a Miyabe H, Asada R, Takemoto Y. Org. Biomol. Chem. 2012; 10: 3519
29b Miller SP, Zhong Y.-L, Liu Z, Simeone M, Yasuda N, Limanto J, Chen Z, Lynch J, Capodanno V. Org. Lett. 2014; 16: 174
29c Takahashi K, Ikura M, Habashita H, Nishizaki M, Sugiura T, Yamamoto S, Nakatani S, Ogawa K, Ohno H, Nakai H, Toda M. Bioorg. Med. Chem. 2005; 13: 4527
29d Chen YK, Yoshida M, MacMillan DW. J. Am. Chem. Soc. 2006; 128: 9328

Supplementary Material

Supporting Information