Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(6): 777-784
DOI: 10.1055/s-0032-1318307
DOI: 10.1055/s-0032-1318307
paper
N-Arylation of Protected Azamacrocycles
Further Information
Publication History
Received: 27 December 2012
Accepted after revision: 02 February 2013
Publication Date:
18 February 2013 (online)
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%).
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are 1H and 13C NMR spectra.
- Supporting Information
-
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