N-Arylation of Protected Azamacrocycles

Alberte X. Veiga; Sven Arenz; Máté Erdélyi

doi:10.1055/s-0032-1318307

Synthesis, Table of Contents

Synthesis 2013; 45(6): 777-784
DOI: 10.1055/s-0032-1318307

paper

N-Arylation of Protected Azamacrocycles

Alberte X. Veiga

Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden Fax: +46(31)7721394 Email: mate@chem.gu.se

,

Sven Arenz

Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden Fax: +46(31)7721394 Email: mate@chem.gu.se

,

Máté Erdélyi*

Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg, Sweden Fax: +46(31)7721394 Email: mate@chem.gu.se

› Author Affiliations

Abstract

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Abstract

A rapid method for efficient palladium-catalyzed N-arylation of polynitrogenated macrocycles is presented. Its applicability for functionalization of protected azamacrocycles of various sizes with substituted aryl bromides of optional electronic properties is demonstrated. The compatibility of the protocol with common N-protecting schemes as well as the impact of electronic versus steric factors is discussed. Using a commercially available catalytic system and easily available alkoxide or phenoxide base, the method provides moderate to excellent yields of N-arylated azamacrocycles (45–96%).

Key words

azamacrocycles - N-arylation - C–N coupling - heterocycles - homogeneous catalysis

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References

References

1a Urbanczyk-Pearson LM, Meade TJ. Nature Prot. 2008; 3: 341
1b Werner EJ, Datta A, Jocher CJ, Raymond KN. Angew. Chem. Int. Ed. 2008; 47: 8568
1c Merebach AE, Tóth É. The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging. Wiley; New York: 2001

2a Häussinger D, Huan J, Grzesiek S. J. Am. Chem. Soc. 2009; 131: 1461
2b Almeida RM, Geraldes CF. G. C, Pauleta SR, Moura JJ. G. Inorg. Chem. 2011; 50: 10600

3a Pershagen E, Nordholm J, Borbás KE. J. Am. Chem. Soc. 2012; 134: 9832
3b Chen T, Wang X, He Y, Zhang C, Wu Z, Liao K, Wang J, Guo Z. Inorg. Chem. 2009; 48: 5801
3c Yu M, Price JR, Jensen P, Lovitt CJ, Shelper T, Duffy S, Windus LC, Avery VM, Rutledge PJ, Todd MH. Inorg. Chem. 2011; 50: 12823

4 Butler SJ, Parker D. Chem Soc. Rev. 2013; 42: 1652

5a Pasquale S, Sattin S, Escudero-Adán EC, Martinez-Belmonte M, de Mendoza J. Nature Commun. 2012; 3: 785
5b Pieters G, Cazzolaro A, Bonomi R, Prins LJ. Chem. Commun. 2012; 48: 1916

6 Krivickas SJ, Tamanini E, Todd MH, Watkinson M. J. Org. Chem. 2007; 72: 8280
7 Michinobu T, Shinoda S, Nakanishi T, Hill JP, Fujii K, Player TN, Tsukube H, Ariga K. Phys. Chem. Chem. Phys. 2011; 13: 4895
8 Li N, English C, Eaton A, Gillespie A, Ence TC, Christensen TJ, Sego A, Harrison RG, Lamb JD. J. Chromatogr., A 2012; 1245: 83
9 Wu W, Lei P, Liu Q, Hu J, Gunn AP, Chen M, Rui Y, Su A, Xie Z, Zhao Y.-F, Bush AI, Li Y. J. Biol. Chem. 2008; 14: 31657
10 Pasey SJ, Sadler PJ. Chem. Commun. 2004; 306
11 Suchý M, Hudson RH. E. Eur. J. Org. Chem. 2008; 73: 4847
12 Ravikumar I, Ghosh P. Chem. Soc. Rev. 2012; 41: 3077
13 Erdélyi M, d’Auvergne E, Navarro-Vázquez A, Leonov A, Griesinger C. Chem. Eur. J. 2011; 17: 9368
14 Bühlmann P, Chen LD. Supramolecular Chemistry: From Molecules to Nanomaterials. Wiley; New York: 2012: 2540
15 Zhang X.-X, Buchwald SL. J. Org. Chem. 2000; 65: 8027

16a Subat M, König B. Synthesis 2001; 1818
16b Stasny V, Lhoták P, Stibor I, König B. Tetrahedron 2006; 62: 5748
16c Nakanishi M, Bolm C. Adv. Synth. Catal. 2006; 348: 1823
16d Burdette SC, Lippard SJ. Inorg. Chem. 2002; 41: 6816
16e Beletskaya IP, Averin AD, Bessmertnykh AG, Denat F, Guilard R. Tetrahedron Lett. 2002; 43: 1193
16f Beletskaya IP, Bessmertnykh AG, Averin AD, Denat F, Guillard R. Eur. J. Org. Chem. 2005; 281
16g Beletskaya IP, Averin AD. Pure Appl. Chem. 2004; 76: 1605

17 Russo F, Odell LR, Olofsson K, Nilsson P, Larhed M In Microwaves in Organic Synthesis . 3rd ed., Vol. 2; de la Hoz A, Loupy A. Wiley-VCH; Weinheim: 2012: 607-671

18a Wan Y, Alterman M, Hallberg A. Synthesis 2002; 1597
18b Sharifi A, Hosseinzadeh R, Mirzaei M. Monatsh. Chem. 2002; 133: 329
18c Loones KT. J, Maes BU. W, Rombouts G, Hostyn S, Diels G. Tetrahedron 2005; 61: 10338

19a Hartwig JF, Richards S, Baranano D, Paul F. J. Am. Chem. Soc. 1996; 118: 3626
19b Baranano D, Hartwig JF. J. Am. Chem. Soc. 1995; 117: 2937

20 Ogawa A, Curran DP. J. Org. Chem. 1997; 62: 450
21 Smith JA, Jones RK, Booker GW, Pyke SM. J. Org. Chem. 2008; 73: 8880
22 Hennings DD, Iwama T, Rawal VH. Org. Lett. 1999; 8: 1205
23 Erdélyi M, Gogoll A. J. Org. Chem. 2001; 66: 4165
24 Tundel RE, Anderson KW, Buchwald SL. J. Org. Chem. 2006; 71: 430
25 Jensen TA, Liang X, Tanner D, Skjaerbaek N. J. Org. Chem. 2004; 69: 4936
26 Schulle II JP, Tweedie SR. Synlett 2007; 2331

27a Alcazar-Roman LM, Hartwig JF. J. Am. Chem. Soc. 2001; 123: 12905
27b Martinelli JR, Clark TP, Watson DA, Munday RH, Buchwald SL. Angew. Chem. Int. Ed. 2004; 46: 8612

28 For ortho-substituted substrates, a β-hybride elimination was observed, as discussed in larger detail in: Muci AR, Buchwald SR. Top. Curr. Chem. 2002; 219: 131

29a Yoo J, Reichert DE, Welch MJ. Chem. Commun. 2003; 766
29b Yoo J, Reichert DE, Welch MJ. J. Med. Chem. 2004; 47: 6625
29c Boldrini V, Giovenzana GB, Pagliarin R, Palmisano G, Sisti M. Tetrahedron Lett. 2000; 41: 6527

30 Kawamura M, Hashihayata T, Sunami S, Sugimoto T, Yamamoto F, Sato Y, Kamijom K, Mitsuya M, Iwasawa Y, Komatani H. (Merck Sharp & Dohme Limited) EP 1790650A1, 2007 .

31a Jablonski L, Billard T, Langois BR. Tetrahedron Lett. 2003; 44: 1055
31b Joubert J, Roussel S, Christophe C, Billard T, Langlois BR, Vidal T. Angew. Chem. Int. Ed. 2003; 42: 3133
31c Jablonski L, Joubert J, Billard T, Langlois BR. Synlett 2003; 230

32 Hyemi K, Kyung-Soo M, Soyoung S, Jinsung T. Chem. Asian J. 2011; 6: 1987
33 Armarego WL. F, Perrin DD. Purification of Laboratory Chemicals . Butterworth Heinemann; Oxford: 2000

34a Woods M, Kiefer GE, Bott S, Castillo-Muzquiz A, Eshelbrenner C, Michaudet L, McMillan K, Mudigunda SD, Ogrin D, Tircsó G, Zhang S, Zhao P, Sherry D. J. Am. Chem. Soc. 2004; 126: 9248
34b Burdette SC, Lippard SJ. Inorg. Chem. 2002; 41: 6816
34c Yang W, Giandomenico CM, Sartori M, Moore DA. Tetrahedron Lett. 2002; 43: 2481
34d Boldrini V, Givenzana GB, Pagliarin R, Palmisano G, Sisti M. Tetrahedron Lett. 2000; 41: 6527
34e Li C, Wong WT. Tetrahedron 2004; 60: 5595
34f Jagadish B, Brickert-Albrecht GL, Nichol GS, Mash EA, Raghunand N. Tetrahedron Lett. 2011; 52: 2058
34g Fabbrizzi L, Foti F, Lichelli M, Maccarini PM, Sacchi D, Zema M. Chem. Eur. J. 2002; 8: 4965
34h Nadler A, Hain C, Diederichsen U. Eur. J. Org. Chem. 2009; 4593

35 Cawley MJ, Cloke FG. N, Fitzmaurice RJ, Pearson SE, Scott JS, Caddick S. Org. Biomol. Chem. 2008; 6: 2820
36 Schön U, Messinger J, Buckendahl M, Prabhu MS, Konda A. Tetrahedron 2009; 65: 8125

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