Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles

Steven Frippiat; Antoine Peresson; Thibaut Perse; Yvan Ramondenc; Cédric Schneider; Olivier Querolle; Patrick Angibaud; Virginie Poncelet; Lieven Meerpoel; Vincent Levacher; Laurent Bischoff; Christine Baudequin; Christophe Hoarau

doi:10.1055/s-0040-1708003

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(10): 1015-1021
DOI: 10.1055/s-0040-1708003

letter

Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles

Steven Frippiat‡

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Antoine Peresson

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Thibaut Perse

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France

,

Yvan Ramondenc

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Cédric Schneider

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Olivier Querolle

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France

,

Patrick Angibaud

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France

,

Virginie Poncelet

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France

,

Lieven Meerpoel

^cJanssen Research & Development, Division of Janssen-Cilag a division of Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium

,

Vincent Levacher

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Laurent Bischoff

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Christine Baudequin∗

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

,

Christophe Hoarau∗

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

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Abstract

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Abstract

The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.

Key words

C–H functionalization - palladium catalysis - imidazole - arylation - alkenylation

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Referenzen

References and Notes

1a Wang W, Tang X, Hua F, Ling T.-J, Wan X.-C, Bao G.-H. Org. Lett. 2018; 20: 2672
1b Rodrigues de Carvalho L, de Brito TV, da Simiao Jr CJ, Dias GJ. Jr, de Aguiar MagalhãresD, Guimarães SousaS, Oliveira SilvaR, Pereira da Silva FR, Pereira VasconcelosD. F, Costa VérasL. M, Leite JR. S. A, Santos MartinsD, da Silva MartinsC, Soares de Oliveira J, Barbosa AL. R. Biomed. Pharmacother. 2018; 102: 278
1c Silva VG, Silva RO, Damasceno SR. B, Carvalho NS, Prudêncio RS, Aragão KS, Guimarães MA, Campos SA, Véras LM. C, Godejohann M, Leite JR. S. A, Barbosa AL. R, Medeiros J.-VR. J. Nat. Prod. 2013; 76: 1071
1d Ding H, Roberts AG, Harran PG. Chem. Sci. 2013; 4: 303
1e Sato S, Iwata F, Takeo J, Kawahara H, Kuramoto M, Uno H. Chem. Lett. 2011; 40: 186
1f De Luca L. Curr. Med. Chem. 2006; 13: 1
1g Iinuma Y, Kozawa S, Ishiyama H, Tsuda M, Fukushi E, Kawabata J, Fromont J, Kobayashi J. J. Nat. Prod. 2005; 68: 1109
1h Fresneda PM, Molina P, Sanz MA. Tetrahedron Lett. 2001; 42: 851

2 Zhang L, Peng X.-M, Damu GL. V, Geng R.-X, Zhou C.-H. Med. Res. Rev. 2014; 34: 340

For recent reviews, see:

3a Chen W.-C, Zhu Z.-L, Lee C.-S. Adv. Opt. Mater. 2018; 6: 1800258
3b Anderson EB, Long TE. Polymer 2010; 51: 2447

For reviews, see:

4a Liu J.-Q, Gou X.-X, Han Y.-F. Chem. Asian J. 2018; 13: 2257
4b Garrison JC, Youngs WJ. Chem. Rev. 2005; 105: 3978
4c Braband H, Kueckmann T, Theresa I, Abram U. J. Organomet. Chem. 2005; 690: 5421
4d Scott NM, Nolan SP. Eur. J. Inorg. Chem. 2005; 1815
4e Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1290

For recent reviews, see:

5a Wang N, Xu J, Lee JK. Org. Biomol. Chem. 2018; 16: 8230
5b Wang Z, Pan D, Li T, Jin Z. Chem. Asian J. 2018; 13: 2149

For leading references, see:

6a Wilkes JS, Zaworotko MJ. J. Chem. Soc., Chem. Commun. 1992; 965
6b Welton T. Chem. Rev. 1999; 99: 2071
6c Wasserscheid P, Keim W. Angew. Chem. Int. Ed. 2000; 39: 3772
6d Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667
6e Karimi B, Tavakolian M, Akbari M, Mansouri F. ChemCatChem 2018; 10: 3173

For recent reviews, see:

7a Rossi R, Angelici G, Casotti G, Manzini C, Lessi M. Adv. Synth. Catal. 2019; 361: 2737
7b Gulevich AV, Dudnik AS, Chernyak N, Gevorgyan V. Chem. Rev. 2013; 113: 3084
7c Kamijo S, Yamamoto Y. Chem. Asian J. 2007; 2: 568

For selected C–H arylation of imidazoles or their ring-fused analogues catalyzed by rhodium, copper, or nickel metals, see:

8a Lewis JC, Berman AM, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2008; 130: 2493
8b Lewis JC, Bergman RG, Ellman JA. Acc. Chem. Res. 2008; 41: 1013
8c Lewis JC, Wu JY, Bergman RG, Ellman JA. Angew. Chem. Int. Ed. 2006; 45: 1589
8d Lewis JC, Wiedemann SH, Bergman RG, Ellman JA. Org. Lett. 2004; 6: 35
8e Zhao D, Wang W, Yang F, Lan J, Yang L, Gao G, You J. Angew. Chem. Int. Ed. 2009; 48: 3296
8f Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
8g Do H.-Q, Khan RM. K, Daugulis O. J. Am. Chem. Soc. 2008; 130: 15185
8h Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2007; 129: 12404
8i Muto K, Hatakeyama T, Yamaguchi J, Itami K. Chem. Sci. 2015; 6: 6792

For reviews on this topic, see:

9a Ref. 7a.
9b Bellina F, Rossi R. Adv. Synth. Catal. 2010; 352: 1223
9c De Ornellas S, Storr TE, Williams TJ, Baumann CG, Fairlamb IJ. S. Curr. Org. Synth. 2011; 8: 79

For palladium-catalyzed intramolecular direct arylation of imidazole, see:

10a Xu X, Zhao L, Li Y, Soulé J.-F, Doucet H. Adv. Synth. Catal. 2015; 357: 2869
10b Laha JK, Dayal N, Singh S, Bhimpuria R. Eur. J. Org. Chem. 2014; 5469
10c Laha JK, Cuny GD. J. Org. Chem. 2011; 76: 8477
10d Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron 2010; 66: 1937
10e Majumdar KC, Debnath P, Taher A, Pal AK. Can. J. Chem. 2008; 86: 325
10f Lee HS, Kim SH, Gowrisankar S, Kim JN. Tetrahedron 2008; 64: 7183
10g Arai N, Takahashi M, Mitani M, Mori A. Synlett 2006; 3170
10h Gracias V, Gasiecki AF, Pagano TG, Djuric SW. Tetrahedron Lett. 2006; 47: 8873
10i Delest B, Tisserand J.-Y, Robert J.-M, Nourrisson M.-R, Pinson P, Duflos M, Le Baut G, Renard P, Pfeiffer B. Tetrahedron 2004; 60: 6079
10j Kuroda T, Suzuki F. Tetrahedron Lett. 1991; 32: 6915

For palladium-catalyzed intermolecular direct arylation of imidazole derivatives, see:

11a Vellakkaran M, Lingayya R, Kumar BN, Nagaiah K, Poornachandra Y, Kumar CG. RSC Adv. 2015; 5: 8057
11b Grosse S, Pillard C, Massip S, Marchivie M, Jarry C, Bernard P, Guillaumet G. J. Org. Chem. 2015; 80: 8539

12a Lessi M, Panzetta G, Marianetti G, Bellina F. Synthesis 2017; 49: 4676
12b Perego LA, Grimaud L, Bellina F. Adv. Synth. Catal. 2016; 358: 597
12c Bellina F, Lessi M, Manzini C. Eur. J. Org. Chem. 2013; 5621
12d Bellina F, Cauteruccio S, Di Fiore A, Marchetti C, Rossi R. Tetrahedron 2008; 64: 6060
12e Bellina F, Cauteruccio S, Di Fiore A, Rossi R. Eur. J. Org. Chem. 2008; 5436
12f Bellina F, Cauteruccio S, Rossi R. Curr. Org. Chem. 2008; 12: 774
12g Bellina F, Calandri C, Cauteruccio S, Rossi R. Tetrahedron 2007; 63: 1970
12h Bellina F, Cauteruccio S, Rossi R. J. Org. Chem. 2007; 72: 8543
12i Bellina F, Cauteruccio S, Mannina L, Rossi R, Viel S. Eur. J. Org. Chem. 2006; 693
12j Bellina F, Cauteruccio S, Mannina L, Rossi R, Viel S. J. Org. Chem. 2005; 70: 3997

13 Joo JM, Touré BB, Sames D. J. Org. Chem. 2010; 75: 4911
14 Kuroda T, Suzuki F. Tetrahedron Lett. 1991; 32: 6915

15a Martin T, Verrier C, Hoarau C, Marsais F. Org. Lett. 2008; 10: 2909
15b Verrier C, Martin T, Hoarau C, Marsais F. J. Org. Chem. 2008; 73: 7383
15c Roger J, Verrier C, Le Goff R, Hoarau C, Doucet H. ChemSusChem 2009; 2: 951
15d Verrier C, Hoarau C, Marsais F. Org. Biomol. Chem. 2009; 7: 647
15e Verrier C, Fiol-Petit C, Hoarau C, Marsais F. Org. Biomol. Chem. 2011; 9: 6215
15f Théveau L, Verrier C, Lassalas P, Martin T, Dupas G, Querolle O, Van Hijfte L, Marsais F, Hoarau C. Chem. Eur. J. 2011; 17: 14451
15g Théveau L, Querolle O, Dupas G, Hoarau C. Tetrahedron 2013; 69: 4375

16 Thireau J, Schneider C, Baudequin C, Gaurrand S, Angibaud P, Meerpoel L, Levacher V, Querolle O, Hoarau C. Eur. J. Org. Chem. 2017; 2491

For recent reviews, see:

17a Cai X.-h, Yang M, Xie B. Curr. Org. Chem. 2018; 22: 1906
17b Zhang T, Wang N.-X, Xing Y. J. Org. Chem. 2018; 83: 7559
17c Hosseinian A, Nasab FA. H, Ahmadi S, Rahmani Z, Vessally E. RSC Adv. 2018; 8: 26383
17d Schwarz J, König B. Green Chem. 2018; 20: 323
17e Perry GJ. P, Larrosa I. Eur. J. Org. Chem. 2017; 3517
17f Wie Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
17g Jin Y, Fu H. Asian J. Org. Chem. 2017; 6: 368
17h Li H, Miao T, Wang M, Li P, Wang L. Synlett 2016; 27: 1635

18a Allin SM, Bowman WR, Elsegood MR. J, McKee V, Karim R, Rahman SS. Tetrahedron 2005; 61: 2689
18b Aldabbagh F, Bowman WR, Mann E, Slawin AM. Z. Tetrahedron 1999; 55: 8111

19 Two regioisomers were obtained. However, concerning this study only methyl N-alkylated imidazole-4-carboxylates were evaluated.

For recent references, see:

20a Baba K, Masuya Y, Chatani N, Tobisu M. Chem. Lett. 2017; 46: 1296
20b Zhou H, Li J, Yang H, Xia C, Jiang G. Org. Lett. 2015; 17: 4628
20c Zhou Y, Gan Z, Su B, Li J, Duan Z, Mathey F. Org. Lett. 2015; 17: 5722
20d Baba K, Tobisu M, Chatani N. Org. Lett. 2015; 17: 70
20e Karthik V, Gupta V, Anantharaman G. Organometallics 2015; 34: 3713
20f Baba K, Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11892
20g Li Z, Zhou H, Xu J, Wu X, Yao H. Tetrahedron 2013; 69: 3281
20h Ma M.-T, Lu J.-M. Tetrahedron 2013; 69: 2102

21 See the Supporting Information for more details.
22 General Procedure for Pd-Catalyzed Intermolecular Direct C2–H Arylation of Methyl N-Benzyl-1H-imidazole 4-carboxylate under Thermic ConditionsMethyl 1-benzyl-1H-imidazole-4-carboxylate (1a, 80 mg, 0.37 mmol, 1 equiv), the requisite halide 2 (1.2 equiv), Pd(OAc)₂ (18 μmol, 5 mol%), PPh₃ (37 μmol, 10 mol%), CuI (0.74 mmol, 2 equiv), and anhydrous DBU (0.74 mmol, 2 equiv) were placed in a dry sealed tube containing a magnetic stir bar. The tube was evacuated and back-filled with nitrogen three times before adding anhydrous 1,4-dioxane (2.5 mL). The tube was sealed and heated to 140 °C for 18 h. The reaction was filtered through a Celite^® pad (washing with DCM and EtOAc). The solvents were removed under reduced pressure, and the crude product was then purified by column chromatography (DCM to DCM/EtOAc, 9:1).
23 Compound 3a was prepared according to the general procedure. The crude product was purified by flash chromatography to afford 3a in 76% yield using the aryl bromide and 95% yield using the aryl iodide as a pale yellow solid; mp 89–90 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.64 (s, 1 H_im, H5), 7.46 (d, J = 8.0 Hz, 2 H_arom), 7.35–7.33 (m, 3 H_benzyl), 7.22 (d, J = 8.0 Hz, 2 H_arom), 7.09–7.07 (m, 2 H_benzyl), 5.19 (s, 2 H), 3.89 (s, 3 H, OMe), 2.38 (s, 3 H, CH₃). ¹³C NMR (75 MHz, CDCl₃): δ = 163.5 (C=O), 149.5 (C2, Cq_im), 139.7 (C4′, Cq_arom), 135.9 (C1′, Cq_benzyl), 132.9 (C4_im, Cq), 129.3 (2 × CH), 129.2 (2 × CH), 129.1 (2 × CH), 128.4 (CH_benzyl), 127.1 (C5, CH_im), 126.9 (2 × CH_benzyl), 126.5 (Cq), 51.8 (OCH₃), 51.0 (NCH₂), 21.4 (CH₃). IR (ATR): 3125, 3079, 2920, 2850, 1689, 1549, 1330, 1227, 1004, 725 cm^–1. HRMS: Anal. Calcd for C₁₉H₁₉N₂O₂ [M + H]⁺: 307.1447; found: 307.1455.

24a Vabre R, Chevot F, Legraverend M, Piguel S. J. Org. Chem. 2011; 76: 9542
24b Vabre R, Legraverend M, Piguel S. Dyes Pigm. 2014; 105: 145
24c Baladi T, Granzhan A, Piguel S. Eur. J. Org. Chem. 2016; 2421

25 Sahnoun S, Messaoudi S, Brion J.-D, Alami M. Eur. J. Org. Chem. 2010; 6097
26 Lee W.-C, Wang T.-H, Ong T.-G. Chem. Commun. 2014; 50: 3671

27a Muselli M, Baudequin C, Perrio C, Hoarau C, Bischoff L. Chem. Eur. J. 2016; 22: 5520
27b Muselli M, Baudequin C, Hoarau C, Bischoff L. Chem. Commun. 2015; 51: 745

28a Gorelsky SI. Coord. Chem. Rev. 2013; 257: 153
28b Gorelsky SI, Lapointe D, Fagnou K. J. Org. Chem. 2012; 77: 658

29 Iaroshenko VO, Gevorgyan A, Mkrtchyan S, Arakelyan K, Grigoryan T, Yedoyan J, Villinger A, Langer P. J. Org. Chem. 2015; 80: 2103

Zusatzmaterial

Supporting Information