Palladium-Catalyzed Double C–H Arylation Reaction: Tandem Synthesis of Benzo[a]imidazo[5,1,2-cd]indolizines from Imidazo[1,2-a]pyridines and o-Dihaloarenes

Abstract

A palladium-catalyzed direct arylation of 2-arylimidazo[1,2-a]pyridines with o-dihaloarenes via double C–H activation is described. The process comprises intermolecular C3-arylation of 2-arylimidazo[1,2-a]pyridines followed by an intramolecular C5-arylation in a highly regioselective fashion, affording benzo[a]imidazo[5,1,2-cd]indolizine derivatives in moderate to good yields.

Key words

palladium - C–H activation - arylation - tandem synthesis - indolizine-fused polycyclics

• References

• 1a Sapsford KE, Berti L, Medintz IL. Angew. Chem. Int. Ed. 2006; 45: 4562 ; Angew. Chem. 2006, 118, 4676
• 1b Davis LD, Raines RT. ACS Chem. Biol. 2008; 3: 142
• 1c Gonçalves MS. T. Chem. Rev. 2009; 109: 190
• 1d Chen X, Pradhan T, Wang F, Kim JS, Yoon J. Chem. Rev. 2012; 112: 1910
• 1e Itoh T. Chem. Rev. 2012; 112: 4541
• 1f Davis LD, Raines RT. ACS Chem. Biol. 2014; 9: 855
• 2a Singh GS, Mmatli EE. Eur. J. Med. Chem. 2011; 46: 5237
• 2b Heugebaert TS. A, Roman BI, Stevens CV. Chem. Soc. Rev. 2012; 41: 5626
• 3 Koubachi J, Kazzouli SE, Bousmina M, Guillaumet G. Eur. J. Org. Chem. 2014; 5119
• 4a Shao N, Pang G.-X, Yan C.-X, Shi G.-F, Cheng Y. J. Org. Chem. 2011; 76: 7458
• 4b Leopoldo M, Lacivita E, Passafiume E, Contino M, Colabufo NA, Berardi F, Perrone R. J. Med. Chem. 2007; 50: 5043
• 4c Laquintana V, Denora N, Lopedota A, Suzuki H, Sawada M, Serra M, Biggio G, Latrofa A, Trapani G, Liso G. Bioconjugate Chem. 2007; 18: 1397
• 5a Firmansyah D, Ciuciu AI, Hugues V, Blanchard-Desce M, Flamigni L, Gryko DT. Chem. Asian J. 2013; 8: 1279
• 5b Kovalska VB, Losytskyy MY, Kryvorotenko DV, Balanda AO, Tokar VP, Yarmoluk SM. Dyes Pigments 2006; 68: 39
• 5c Farsi Baf MM, Pordel M, Daghigh LR. Tetrahedron Lett. 2014; 55: 6925
• 6a Li J, Hu G, Li X, Hu B, Wang N, Lu P, Wang Y. Eur. J. Org. Chem. 2013; 7320
• 6b Seferoğlu Z, Ihmels H, Şahin E. Dyes Pigments 2015; 113: 465
• 7a Mutai T, Tomoda H, Ohkawa T, Yabe Y, Araki K. Angew. Chem. Int. Ed. 2008; 47: 9522 ; Angew. Chem. 2008, 120, 9664
• 7b Stasyuk AJ, Banasiewicz M, Cyranski MK, Gryko DT. J. Org. Chem. 2012; 77: 5552
• 7c Stasyuk AJ, Banasiewicz M, Ventura B, Cyrański MK, Gryko DT. New J. Chem. 2014; 38: 189
• 7d Shono H, Ohkawa T, Tomoda H, Mutai T, Araki K. ACS Appl. Mater. Interfaces 2011; 3: 654
• 8a Gudmundsson KS, Drach JC, Townsend LB. Tetrahedron Lett. 1996; 37: 6275
• 8b El Kazzouli S, Griffon du Bellay A, Berteina-Raboin S, Delagrange P, Caignard D.-H, Guillaumet G. Eur. J. Med. Chem. 2011; 46: 4252
• 9 Hervet M, Théry I, Gueiffier A, Enguehard-Gueiffier C. Helv. Chim. Acta 2003; 86: 3461
• 10a Enguehard C, Renou J.-L, Collot V, Hervet M, Rault S, Gueiffier A. J. Org. Chem. 2000; 65: 6572
• 10b Crozet MD, Castera-Ducros C, Vanelle P. Tetrahedron Lett. 2006; 47: 7061
• 10c El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Lett. Org. Chem. 2012; 9: 118
• 10d Bazin M.-A, Marhahour S, Tonnerre A, Marchand P. Tetrahedron Lett. 2013; 54: 5378
• 11a Hervet M, Théry I, Gueiffier A, Enguehard-Gueiffier C. Helv. Chim. Acta 2003; 86: 3461
• 11b Enguehard-Gueiffier C, Croix C, Hervet M, Kazock J.-Y, Gueiffier A, Abarbri M. Helv. Chim. Acta 2007; 90: 2349
• 12a Andaloussi M, Chezal JM, Moreau E, Lartigue C, El Laghdach A, Teulade JC, Chavignon O. Heterocycles 2005; 65: 1071
• 12b El Kazzouli S, Berthault A, Berteina-Raboin S, Mouaddib A, Guillaumet G. Lett. Org. Chem. 2005; 2: 184
• 12c Oudot R, Costes P, Allouchi H, Pouvreau M, Abarbri M, Gueiffier A, Enguehard-Gueiffier C. Tetrahedron 2011; 67: 9576
• 12d Bahlaouan Z, Abarbri M, Duchéne A, Thibonnet J, Henry N, Enguehard-Gueiffier C, Gueiffier A. Org. Biomol. Chem. 2011; 9: 1212
• 12e Henry N, Thiery E, Petrignet J, Halouchi H, Thibonnet J, Abarbri M. Eur. J. Org. Chem. 2012; 6212
• 13a Enguehard C, Allouchi H, Gueiffier A, Buchwald SL. J. Org. Chem. 2003; 68: 4367
• 13b Enguehard C, Thery I, Gueiffier A, Buchwald SL. Tetrahedron 2006; 62: 6042
• 13c El Akkaoui A, Hiebel M.-A, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron 2012; 68: 9131

For selected recent reviews, see:
• 14a Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 14b Seregin I.-V, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
• 14c Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792 ; Angew. Chem. 2009, 121, 9976
• 14d Bellina F, Rossi R. Tetrahedron 2009; 65: 10269
• 14e Daugulis O. Top. Curr. Chem. 2010; 292: 57
• 14f Rossi R, Bellina F, Lessi M, Manzini C. Adv. Synth. Catal. 2014; 356: 17
• 15a Koubachi J, El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Synlett 2006; 3237
• 15b Touré BB, Lane BS, Sames D. Org. Lett. 2006; 8: 1979
• 15c Cao H, Zhan H, Lin Y, Lin X.-L, Du Z, Jiang H. Org. Lett. 2012; 14: 1688
• 15d Fu H.-Y, Chen L, Doucet H. J. Org. Chem. 2012; 77: 4473
• 15e Fu H.-Y, Zhao L, Bruneau C, Doucet H. Synlett 2012; 23: 2077
• 15f Belkessam F, Derridj F, Zhao L, Elias A, Aidene M, Djebbar S, Doucet H. Tetrahedron Lett. 2013; 54: 4888
• 15g Martin RA, Chartoine A, Slawin AM. Z, Nolan SP. Beilstein J. Org. Chem. 2012; 8: 1637
• 15h Kumar P.-V, Lin W.-S, Shen J.-S, Nandi D, Lee HM. Organometallics 2011; 30: 5160
• 15i Cao H, Lin Y, Zhan H, Du Z, Lin X, Liang Q.-M, Zhang H. RSC Adv. 2012; 2: 5972
• 15j Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G. Tetrahedron 2010; 66: 1937
• 16a Koubachi J, El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. Synthesis 2008; 2537
• 16b Koubachi J, Berteina-Raboin S, Mouaddib A, Guillaumet G. Synthesis 2009; 271
• 17a Fukuyama T, Chatani N, Kakiuchi F, Murai S. J. Am. Chem. Soc. 1996; 118: 493
• 17b Chatani N, Ie Y, Kakiuchi F, Murai S. J. Org. Chem. 1997; 62: 2604
• 17c Fukuyama T, Chatani N, Tatsumi J, Kakiuchi F, Murai S. J. Am. Chem. Soc. 1998; 120: 11522
• 17d Chatani N, Fukuyama T, Tatamidani H, Kakiuchi F, Murai S. J. Org. Chem. 2000; 65: 4039

Selected recent examples:
• 18a Joo JM, Touré BB, Sames D. J. Org. Chem. 2010; 75: 4911
• 18b Shibahara F, Yamaguchi E, Murai T. J. Org. Chem. 2011; 76: 2680
• 18c Takfaoui A, Zhao L, Touzani R, Soulé J.-F, Dixneuf PH, Doucet H. Tetrahedron 2014; 70: 8316
• 18d Joo JM, Guo P, Sames D. J. Org. Chem. 2013; 78: 738
• 18e Shibahara F, Yamaguchi T, Yamaguchi E, Murai T. J. Org. Chem. 2012; 77: 8815
• 18f Yamaguchi E, Shibahara F, Murai T. Chem. Lett. 2011; 40: 939
• 19a Petit A, Flygare J, Miller AT, Winkel G, Ess DH. Org. Lett. 2012; 14: 3680
• 19b Gorelsky SI. Coord. Chem. Rev. 2013; 257: 153
• 20a Koubachi J, El Kazzouli S, Berteina-Raboin S, Mouaddib A, Guillaumet G. J. Org. Chem. 2007; 72: 7650
• 20b Marhadour S, Bazin M.-A, Marchand P. Tetrahedron Lett. 2012; 53: 297
• 20c Pericherla K, Khedar P, Khungar B, Kumar A. Chem. Commun. 2013; 49: 2924
• 20d Gembus V, Bonfanti J.-F, Querolle O, Jubault P, Levacher V, Hoarau C. Org. Lett. 2012; 14: 6012
• 21a Li W, Nelson DP, Jensen MS, Hoerrner RS, Javadi GJ, Cai D, Larsen RD. Org. Lett. 2003; 5: 4835
• 21b El Akkaoui A, Berteina-Raboin S, Mouaddib A, Guillaumet G. Eur. J. Org. Chem. 2010; 862
• 21c Huang C, Giokaris A, Gevorgyan V. Chem. Lett. 2011; 40: 1053
• 21d Pellegatti L, Vedrenne E, Leger J.-M, Jarry C, Routier S. J. Comb. Chem. 2010; 12: 604
• 21e Gauthier DR. Jr, Limanto J, Devine PN, Desmond RA, Szumigala RH. Jr, Foster BS, Volante RP. J. Org. Chem. 2005; 70: 5938
• 21f Huang S, Qing J, Wang S, Wang H, Zhang L, Tang Y. Org. Biomol. Chem. 2014; 12: 2344
• 21g Zhu Y, Shi B, Fang R, Wang X, Jiang H. Org. Biomol. Chem. 2014; 12: 5773
• 21h Wang J.-X, McCubbin JA, Jin M, Laufer RS, Mao Y, Crew AP, Mulvihill MJ, Snieckus V. Org. Lett. 2008; 10: 2923
• 21i Guchhait SK, Kandekar S, Kashyap M, Taxak N, Bharatam PV. J. Org. Chem. 2012; 77: 8321
• 21j Roman DS, Poiret V, Pelletier G, Charette AB. Eur. J. Org. Chem. 2015; 67
• 22a Peng J, Chen T, Chen C, Li B. J. Org. Chem. 2011; 76: 9507
• 22b Peng J, Shang G, Chen C, Miao Z, Li B. J. Org. Chem. 2013; 78: 1242
• 22c Chen C, Shang G, Zhou J, Yu Y, Li B, Peng J. Org. Lett. 2014; 16: 1872
• 23 Aginagalde M, Vara Y, Arrieta A, Zangi R, Cebolla VL, Delgado-Camón A, Cossío FP. J. Org. Chem. 2010; 75: 2776
• 24a Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338 ; Angew. Chem. 2008, 120, 6438
• 24b Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
• 25a Ackermann L. Chem. Rev. 2011; 111: 1315
• 25b Lafrance M, Fagnou K. J. Am. Chem. Soc. 2006; 128: 16496
• 26 Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M. Bull. Chem. Soc. Jpn. 1998; 71: 467
• 27 Pericherla K, Kaswan P, Khedar P, Khungar B, Parang K, Kumar A. RSC Adv. 2013; 3: 18923