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Synthesis 2012; 44(14): 2264-2276
DOI: 10.1055/s-0031-1291124
DOI: 10.1055/s-0031-1291124
paper
Palladium-Catalysed Direct Arylation of Heteroaromatics Using Unprotected Iodoanilines with Inhibition of the Amination Reaction
Further Information
Publication History
Received: 19 March 2012
Accepted after revision: 18 April 2012
Publication Date:
13 June 2012 (online)
Abstract
The palladium-catalysed direct arylation of heteroaromatics with unprotected iodoanilines proceeds in moderate to high yields using only 1 mol% Pd(OAc)2 as the catalyst and potassium acetate as the base. No amination reaction was observed under these conditions. A wide variety of heteroarenes have been successfully employed.
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References
- 1 Lednicer D. Bicyclic Fused Heterocycles. In The Organic Chemistry of Drug Synthesis. Vol. 7. John Wiley & Sons; Hoboken: 2007
- 2a Akita Y, Inoue A, Yamamoto K, Ohta A, Kurihara T, Shimizu M. Heterocycles 1985; 23: 2327
- 2b Ohta A, Akita Y, Ohkuwa T, Chiba M, Fukunaga R, Miyafuji A, Nakata T, Tani N, Aoyagi Y. Heterocycles 1990; 31: 1951
- 2c Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 2d Satoh T, Miura M. Chem. Lett. 2007; 36: 200
- 2e Campeau L.-C, Stuart DR, Fagnou K. Aldrichimica Acta 2007; 40: 35
- 2f Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
- 2g Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949
- 2h Ackermann L, Vicente R, Kapdi A. Angew. Chem. Int. Ed. 2009; 48: 9792
- 2i Bellina F, Rossi R. Tetrahedron 2009; 65: 10269
- 2j Roger J, Gottumukkala AL, Doucet H. ChemCatChem 2010; 2: 20
- 2k Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
- 2l Fischmeister C, Doucet H. Green Chem. 2011; 13: 741
- 3a Parisien M, Valette D, Fagnou K. J. Org. Chem. 2005; 70: 7578
- 3b Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
- 3c Dwight TA, Rue NR, Charyk D, Josselyn R, DeBoef B. Org. Lett. 2007; 9: 3137
- 3d Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Synthesis 2008; 136
- 3e Smaliy RV, Beaupérin M, Cattey H, Meunier P, Hierso J.-C, Roger J, Doucet H, Coppel Y. Organometallics 2009; 28: 3152
- 3f Roger J, Doucet H. Adv. Synth. Catal. 2009; 351: 1977
- 3g Dong JJ, Roger J, Pozgan F, Doucet H. Green Chem. 2009; 11: 1832
- 3h Ionita M, Roger J, Doucet H. ChemSusChem 2010; 3: 367
- 3i Roger J, Pozgan F, Doucet H. Adv. Synth. Catal. 2010; 352: 696
- 3j Liegault B, Petrov I, Gorelsky SI, Fagnou K. J. Org. Chem. 2010; 75: 1047
- 3k Roy D, Mom S, Beaupérin M, Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2010; 49: 6650
- 3l Franchi L, Rinaldi M, Vignaroli G, Innitzer A, Radi M, Botta M. Synthesis 2010; 3927
- 3m Lapointe D, Markiewicz T, Whipp CJ, Toderian A, Fagnou K. J. Org. Chem. 2011; 76: 749
- 4a Okazawa T, Satoh T, Miura M, Nomura M. J. Am. Chem. Soc. 2002; 124: 5286
- 4b Hassan J, Gozzi C, Schulz E, Lemaire M. J. Organomet. Chem. 2003; 687: 280
-
4c Masui K, Ikegami H, Mori A. J. Am. Chem. Soc. 2004; 126: 5074
-
4d Kobayashi K, Sugie A, Takahashi M, Masui K, Mori A. Org. Lett. 2005; 7: 5083
- 4e David E, Pellet-Rostaing S, Lemaire M. Tetrahedron 2007; 63: 8999
- 4f Amaladass P, Clement JA, Mohanakrishnan AK. Tetrahedron 2007; 63: 10363
- 4g Chiong HA, Daugulis O. Org. Lett. 2007; 9: 1449
- 4h Nakano M, Tsurugi H, Satoh T, Miura M. Org. Lett. 2008; 10: 1851
- 4i Derridj F, Roger J, Geneste F, Djebbar S, Doucet H. J. Organomet. Chem. 2009; 694: 455
- 4j Yanagisawa S, Ueda K, Sekizawa H, Itami K. J. Am. Chem. Soc. 2009; 131: 14622
- 4k Liégault B, Lapointe D, Caron L, Vlassova A, Fagnou K. J. Org. Chem. 2009; 74: 1826
- 4l Dong JJ, Roger J, Doucet H. Tetrahedron Lett. 2009; 50: 2778
- 4m Shibahara F, Yamaguchi E, Murai T. Chem. Commun. 2010; 46: 2471
- 4n Dong JJ, Doucet H. Eur. J. Org. Chem. 2010; 611
- 4o Ueda K, Yanagisawa S, Yamaguchi J, Itami K. Angew. Chem. Int. Ed. 2010; 49: 8946
- 4p Roger J, Požgan F, Doucet H. Adv. Synth. Catal. 2010; 352: 696
- 4q Laidaoui N, Miloudi A, El Abed D, Doucet H. Synthesis 2010; 2553
- 4r Rene O, Fagnou K. Org. Lett. 2010; 12: 2116
- 4s Beydoun K, Doucet H. ChemSusChem 2011; 4: 526
- 4t Chen L, Roger J, Bruneau C, Dixneuf PH, Doucet H. Chem. Commun. 2011; 47: 1872
- 4u Schipper DJ, Fagnou K. Chem. Mater. 2011; 23: 1594
- 5a Yokooji A, Okazawa T, Satoh T, Miura M, Nomura M. Tetrahedron 2003; 59: 5685
-
5b Kobayashi K, Mohamed A, Mohamed S, Mori A. Tetrahedron 2006; 62: 9548
- 5c Campeau L.-C, Bertrand-Laperle M, Leclerc J.-P, Villemure E, Gorelsky S, Fagnou K. J. Am. Chem. Soc. 2008; 130: 3276
- 6a Hoarau C, Du Fou de Kerdaniel A, Bracq N, Grandclaudon P, Couture A, Marsais F. Tetrahedron Lett. 2005; 46: 8573
- 6b Turner GL, Morris JA, Greaney MF. Angew. Chem. Int. Ed. 2007; 46: 7996
- 6c Ohnmacht SA, Mamone P, Culshaw AJ, Greaney MF. Chem. Commun. 2008; 1241
- 6d Besselievre F, Mahuteau-Betzer F, Grierson DS, Piguel S. J. Org. Chem. 2008; 73: 3278
- 6e Fall Y, Reynaud C, Doucet H, Santelli M. Eur. J. Org. Chem. 2009; 4041
- 6f Dong JJ, Roger J, Verrier C, Martin T, Le Goff R, Hoarau C, Doucet H. Green Chem. 2010; 12: 2053
- 7a Olsen CA, Parera N, Albericio F, Alvarez M. Tetrahedron Lett. 2005; 46: 2041
- 7b Pla D, Marchal A, Olsen CO, Albericio F, Alvarez M. J. Org. Chem. 2005; 70: 8231
- 7c Arai N, Takahashi M, Mitani M, Mori A. Synlett 2006; 3170
- 7d Joucla L, Popowycz F, Lozach O, Meijer L, Joseph B. Helv. Chim. Acta 2007; 90: 753
- 7e Fall Y, Doucet H, Santelli M. ChemSusChem 2009; 2: 153
- 7f Nadres ET, Lazareva A, Daugulis O. J. Org. Chem. 2011; 76: 471
- 8 For palladium-catalysed amination reactions, see: Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
- 9a Alagille D, Baldwin RM, Tamagnan GD. Tetrahedron Lett. 2005; 46: 1349
- 9b Zhuravlev FA. Tetrahedron Lett. 2006; 47: 2929
- 10a Franchi L, Rinaldi M, Vignaroli G, Innitzer A, Radi M, Botta M. Synthesis 2010; 3927
- 10b Ioannidou HA, Koutentis PA. Org. Lett. 2011; 13: 1510
- 11a Cerna I, Pohl R, Hocek M. Chem. Commun. 2007; 4729
- 11b Storr TE, Firth AG, Wilson K, Darley K, Baumann CG, Fairlamb IJ. S. Tetrahedron 2008; 64: 6125
- 11c Cerna I, Pohl R, Klepetarova B, Hocek M. J. Org. Chem. 2008; 73: 9048
- 11d Storr TE, Baumann CG, Thatcher RJ, DeOrnellas S, Whitwood AC, Fairlamb IJ. S. J. Org. Chem. 2009; 74: 5810
- 11e Sahnoun S, Messaoudi S, Brion J.-D, Alami M. Org. Biomol. Chem. 2009; 7: 4271
- 11f Cerna I, Pohl R, Klepetarova B, Hocek M. J. Org. Chem. 2010; 75: 2302
- 11g Storr TE, Strohmeier JA, Baumann CG, Fairlamb IJ. S. Chem. Commun. 2010; 46: 6470
- 11h Derridj F, Roger J, Djebbar S, Doucet H. Org. Lett. 2010; 12: 4320
- 11i Derridj F, Roger J, Djebbar S, Doucet H. Adv. Synth. Catal. 2012; 354: 747
For selected recent examples of palladium-catalysed direct arylations of furans, see:
For selected recent examples of palladium-catalysed direct arylations of thiophenes, see:
For selected recent examples of palladium-catalysed direct arylations of thiazoles, see:
For selected recent examples of palladium-catalysed direct arylations of oxazoles or isoxazoles, see:
For selected recent examples of palladium-catalysed direct arylations of pyrroles, see:
For palladium-catalysed direct 2-arylations of oxazole or thiazole derivatives using unprotected haloanilines, see:
For palladium-catalysed direct 5-arylations of a furan or an isothiazole with unprotected haloanilines, see:
For direct arylation reactions using heteroaromatics bearing unprotected substituents, see: