Palladium-Catalyzed Cross-Coupling of 1,4-Disubstituted 5-Iodo-1,2,3-tri­azoles with Organotin Reagents

Abstract

In a new synthetic approach for building systems bearing a 1,2,3-triazole moiety, we report here the first Stille cross-coupling reaction of 1,4-disubstituted 5-iodo-1,2,3-triazoles with a range of stannyl derivatives to give the corresponding 5-vinyl-1,2,3-triazoles.

Key words

1,2,3-triazoles - click chemistry - palladium catalyst - Stille cross-coupling reaction - vinyltin reagents

• References


For 1,2,3-triazoles used for biotechnology applications see:
• 1a Angell YL, Burgess K. Chem. Soc. Rev. 2007; 36: 1674
• 1b Dondoni A. Chem. Asian J. 2007; 2: 700
• 1c Lutz J.-F, Zarafshani Z. Adv. Drug Delivery Rev. 2008; 60: 958
• 1d Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
• 1e Aragao-Leoneti V, Campo VL, Gomes AS, Field RA, Carvalho I. Tetrahedron 2010; 66: 9475
• 1f Kalesh KA, Shi H, Ge J, Yao SQ. Org. Biomol. Chem. 2010; 8: 1749
• 1g Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696

For 1,2,3-triazoles applied to materials sciences see:
• 2a Aprahamian I, Miljanic OS, Dichtel WR, Isoda K, Yasuda T, Kato T, Stoddart JF. Bull. Chem. Soc. Jpn. 2007; 80: 1856
• 2b Fournier D, Hoogenboom R, Schubert US. Chem. Soc. Rev. 2007; 36: 1369
• 2c Lutz J.-F. Angew. Chem. Int. Ed. 2007; 46: 1018
• 2d Iha RK, Wooley KL, Nystrom AM, Burke DJ, Kade MJ, Hawker CJ. Chem. Rev. 2009; 109: 5620

For general information on 1,2,3-triazoles see:
• 3a Lahann J. Click Chemistry for Biotechnology and Materials Science 2009
• 3b Special Issue: Chem. Soc. Rev. 2010; 39: 1221-1408
• 4 Alvarez R, Velazquez S, San-Felix A, Aquaro S, DeClercq E, Perno C.-F, Karlsson A, Balzarini J, Camarasa MJ. J. Med. Chem. 1994; 37: 4185
• 5 Genin MJ, Allwine DA, Anderson DJ, Barbachyn MR, Emmert DE, Garmon SA, Graber DR, Grega KC, Hester JB, Hutchinson DK, Morris J, Reischer RJ, Ford CW, Zurenko GE, Hamel JC, Schaadt RD, Stapert D, Yagi BH. J. Med. Chem. 2000; 43: 953
• 6a Link AJ, Tirell DA. J. Am. Chem. Soc. 2003; 125: 11164
• 6b Seo TS, Li Z, Ruparel H, Ju J. J. Org. Chem. 2003; 68: 609
• 6c Moorhouse AD, Santos AM, Gunaratnam M, Moore M, Neidle S, Moses JE. J. Am. Chem. Soc. 2006; 128: 15972
• 6d Hong V, Presolski SI, Ma C, Finn MG. Angew. Chem. Int. Ed. 2009; 48: 9879
• 7a Bastero A, Font D, Pericàs MA. J. Org. Chem. 2007; 72: 2460
• 7b Chassaing S, Kumarraja M, Sido AS. S, Pale P, Sommer J. Org. Lett. 2007; 9: 883
• 8a Thibault RJ, Takizawa K, Lowenheilm P, Helms B, Mynar JL, Fréchet JM. J, Hawker CJ. J. Am. Chem. Soc. 2006; 128: 12084
• 8b Lutz JF. Angew. Chem. Int. Ed. 2007; 46: 1018
• 8c Nandivada H, Jiang XW, Lahann J. Adv. Mater. (Weinheim, Ger.) 2007; 19: 2197
• 8d Antoni P, Robb MJ, Campos L, Montanez M, Hult A, Malmstrom E, Malkoch M, Hawker CJ. Macromolecules 2010; 43: 6625
• 8e Schwartz E, Breitenkamp K, Fokin VV. Macromolecules 2011; 44: 4735
• 9a Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
• 9b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 9c Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
• 9d Bock VC, Hiemstra H, Van Maarseveen JH. Eur. J. Org. Chem. 2006; 51
• 9e Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 295
• 9f Appukkuttan P, Van der Eycken E. Eur. J. Org. Chem. 2008; 1133
• 9g Kappe CO, Van der Eycken E. Chem. Soc. Rev. 2010; 39: 1280
• 10a Wu Y.-M, Deng J, Li YL, Chen Q.-Y. Synthesis 2005; 1314
• 10b Li L, Zhang G, Zhu A, Zhang L. J. Org. Chem. 2008; 73: 3630
• 10c Brotherton WS, Clark RJ, Zhu L. J. Org. Chem. 2012; 77: 6443
• 11 Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed. 2009; 48: 8081
• 12a Comprehensive Organic Synthesis . Vol. 4. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 865-906
• 12b Nozaki H. Organometallics in Synthesis . Chap. 8. Schlosser M. John Wiley; Chichester: 1994: 535-578
• 12c Tsuji J. Transition Metal Reagents and Catalysts: Innovation in Organic Synthesis. Wiley; Chichester: 1995
• 12d Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998
• 13a Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E. Wiley-Interscience; New York: 2002
• 13b Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. Wiley; Chichester: 2004
• 14a Samuelsson B. Angew. Chem., Int. Ed. Engl. 1983; 22: 805
• 14b Heathcock CH In The Total Synthesis of Natural Products . Vol. 7. Apsimon J. Wiley; New York: 1988
• 14c Ronning IE, Frank HA. J. Food Prot. 1988; 51: 1643
• 14d Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442

For palladium-catalyzed reactions see:
• 15a Deng J, Wu Y.-M, Chen Q.-Y. Synthesis 2005; 2730
• 15b Panteleev J, Geyer K, Aguilar-Aguilar A, Wang L, Lautens M. Org. Lett. 2010; 12: 5092
• 15c Schulman JM, Friedman AA, Panteleev J, Lautens M. Chem. Commun. 2012; 48: 55
• 15d Zhang L, Li Z, Wang X.-J, Yee N, Senanayake CH. Synlett 2012; 23: 1052

For palladium-free reactions see:
• 16a Gerard B, Ryan J, Beeler AB, Porco JA. Jr. Tetrahedron 2006; 62: 6405
• 16b Yang D, Fu N, Liu Z, Li Y, Chen B. Synlett 2007; 278
• 16c Alonso F, Moglie Y, Radivoy G, Yus M. Synlett 2012; 23: 2179
• 17 Pereyre M, Quintard JP, Rahm A. Tin in Organic Synthesis . Butterworths; London: 1987
• 18a Ito S, Hirata Y, Nagatomi Y, Satoh A, Suzuki G, Kimura T, Satow A, Maehara S, Hikichi H, Hata M, Ohta H, Kawamoto H. Bioorg. Med. Chem. Lett. 2009; 19: 5310
• 18b Germain H, Harris CS, Lebraud H. Tetrahedron Lett. 2011; 52: 6376
• 18c Fujinaga M, Maeda J, Yui J, Hatori A, Yamasaki T, Kawamura K, Kumata K, Yoshida Y, Nagai Y, Higuchi M, Suhara T, Fukumura T, Zhang M.-R. J. Neurochem. 2012; 121: 115
• 19a Allgeier H, Auberson Y, Carcache D, Floersheim P, Guibourdenche C, Froestl W, Kallen J, Koller M, Mattes H, Nozulak J, Orain D, Renaud J. WO 2006108591, 2006
• 19b Hansen P, Lawitz K, Lepistoe M, Loenn H, Ray A. WO 2007129962, 2007
• 19c Seefeld MA, Rouse MB, Heerding DA, Peace S, Yamashita DS, McNulty KC. WO 2008098104, 2008
• 20a Malnuit V, Duca M, Manout A, Bougrin K, Benhida R. Synlett 2009; 2123
• 20b Cebrián C, de Cózar A, Prieto P, Díaz-Ortiz A, de la Hoz A, Carrillo JR, Rodriguez AM, Montilla F. Synlett 2010; 55
• 20c Shan Z, Peng M, Fan H, Lu Q, Lu P, Zhao C, Chen Y. Bioorg. Med. Chem. Lett. 2011; 21: 1731
• 20d Ostrowski T, Januszczyk P, Cieslak M, Kazmierczak-Baranska J, Nawrot B, Bartoszak-Adamska E, Zeidler J. Bioorg. Med. Chem. 2011; 19: 4386
• 21 Seyferth D, Stone FG. A. J. Am. Chem. Soc. 1957; 79: 515
• 22 Leusink AJ, Budding HA. J. Organomet. Chem. 1968; 11: 533
• 23a Labadie JW, Stille JK. J. Am. Chem. Soc. 1983; 105: 6129
• 23b Prinz P. Dissertation . Universität Göttingen; Germany: 1996
• 24 Harrowven DC, Curran DP, Kostiuk SL, Wallis-Guy IL, Whiting S, Stenning KJ, Tang B, Packard E, Nanson L. Chem. Commun. 2010; 46: 6335
• 25a Polin J, Schottenberger H. Org. Synth. Coll. Vol. IX . John Wiley & Sons; London: 1998: 411
• 25b Gorgues A, Le Coq A. Org. Synth. 1979; 59: 10
• 26 Cunico RF, Clayton FJ. J. Org. Chem. 1976; 41: 1480
• 27 García-Álvarez J, Díez J, Gimeno J. Green Chem. 2010; 12: 2127