RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2013; 24(4): 412-423
DOI: 10.1055/s-0032-1317944
DOI: 10.1055/s-0032-1317944
account
Regioselective Suzuki–Miyaura Reactions of Aromatic Bis-triflates: Electronic versus Steric Effects
Weitere Informationen
Publikationsverlauf
Received: 09. Oktober 2012
Accepted after revision: 04. Dezember 2012
Publikationsdatum:
11. Januar 2013 (online)
Dedicated to Professor Dr. Viqar Uddin Ahmad on his 72th birthday
Abstract
Suzuki–Miyaura reactions of aromatic bis-triflates, readily available from the corresponding hydroxylated arenes, often proceed with excellent regioselectivity and provide a convenient approach to various arylated benzene derivatives, such as biphenyls, terphenyls, and arylated benzophenones, naphthalenes, xanthones, flavones, coumarins, anthraquinones, tetralones, and fluorenones. The regioselectivity is controlled by steric and electronic parameters and strongly depends on the structure of the substrates.
1 Introduction
2 Benzoates, Phthalates, and Naphthoates
3 Benzophenones and Diphenyl Sulfones
4 Xanthones and Thioxanthones
5 Flavones and Coumarins
6 Anthraquinones, Tetralones, and Fluorenones
7 Conclusion
-
References
- 1 Suzuki A. Pure Appl. Chem. 1985; 57: 1749
- 2a Beller M, Bolm C. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. 2nd ed.. Vols. 1-2. Wiley-VCH; Weinheim: 2004
- 2b de Meijere A, Diederich F. Metal-Catalyzed Cross-Coupling Reactions . 2nd ed. Vols. 1–2. Wiley-VCH; Weinheim: 2004
- 2c Negishi E.-i. Handbook of Organopalladium for Organic Synthesis . Vols. 1-2. Wiley-Interscience; New York: 2002
- 2d Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
- 2e Tsuji J. Palladium Reagents and Catalysts . 2nd ed. Wiley; Chichester: 2004
- 2f Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
- 2g Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
- 2h Roglans A, Pla-Quintana A, Moreno-Manas M. Chem. Rev. 2006; 106: 4622
- 2i Ackermann L. Modern Arylation Methods . Wiley-VCH; Weinheim: 2009
- 2j Wu XF, Anberasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
- 3a King AO, Yasuda N. Organometallics in Process Chemistry . Larsen RD. Springer; Berlin: 2004
- 3b Miyaura N. Top. Curr. Chem. 2002; 219: 11
- 3c Suzuki A. Modern Arene Chemistry . Astruc D. Wiley-VCH; Weinheim: 2002
- 3d Suzuki A. J. Organomet. Chem. 2002; 653: 54
- 4a Proutiere F, Aufiero M, Schoenebeck F. J. Am. Chem. Soc. 2012; 134: 606
- 4b Proutiere FSchoenebeck F. Synlett 2012; 23: 645
- 4c Rossi R, Bellina F, Lessi M. Adv. Synth. Catal. 2012; 354: 1181
- 4d Muller TJ. J. Synthesis 2012; 44: 159
- 4e Proutiere F, Schoenebeck F. Angew. Chem. Int. Ed. 2011; 50: 8192
- 4f Schröter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
- 5a Nishiyama M, Yamamoto T, Koie Y. Tetrahedron Lett. 1998; 39: 617
- 5b Zapf A, Jackstell R, Rataboul F, Riermeier T, Monsees A, Fuhrmann C, Shaikh N, Dingerdissen U, Beller M. Chem. Commun. (Cambridge) 2004; 38
- 5c Rataboul F, Zapf A, Jackstell R, Harkal S, Riermeier T, Monsees A, Dingerdissen U, Beller M. Chem. Eur. J. 2004; 10: 2983
- 5d Wolfe JP, Tomori H, Sadighi JP, Yin J, Buchwald SL. J. Org. Chem. 2000; 65: 1158
- 6a Kamikawa T, Hayashi T. Tetrahedron Lett. 1997; 38: 7087
- 6b Littke AF, Dai CY, Fu GC. J. Am. Chem. Soc. 2000; 122: 4020
- 6c Roy AH, Hartwig JF. Organometallics 2004; 23: 194
- 6d Espinet P, Echavarren AM. Angew. Chem. Int. Ed. 2004; 43: 4704
- 6e Espino G, Kurbangalieva A, Brown JM. Chem. Commun. (Cambridge) 2007; 1742 ; and references cited therein
- 6f Hassan Z, Hussain M, Villinger A, Langer P. Tetrahedron 2012; 68: 6305
- 6g Hassan Z, Hussain M, Langer P. Synlett 2011; 1827
- 7a Schnürch M, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 3283
- 7b Wang R, Manabe K. Synthesis 2009; 1405
- 7c See also ref. 4f.
- 7d Handy ST, Zhang Y. Chem. Commun. (Cambridge) 2006; 299
- 8a Zhang L, Meng T, Wu J. J. Org. Chem. 2007; 72: 9346
- 8b See also ref. 6b.
- 8c Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 20: 3437
- 8d Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 8e Suzuki A. J. Organomet. Chem. 2002; 653: 83
- 9 Appel B, Rotzoll S, Kranich R, Reinke H, Langer P. Eur. J. Org. Chem. 2006; 3638
- 10 For consecutive palladium-catalyzed coupling reactions of halogenated aromatic triflates, see ref. 4a and references cited therein.
- 11 Nawaz M, Ibad MF, Obaid-Ur-Rahman A, Khera RA, Villinger A, Langer P. Synlett 2010; 150
- 12 Nawaz M, Ullah I, Obaid-Ur-Rahman A, Ali A, Patonay T, Villinger A, Langer P. Can. J. Chem. 2012; 10.1139/cjc-2012-0201
- 13 Ibad MF, Obaid-Ur-Rahman A, Nawaz M, Adeel M, Villinger A, Langer P. Synlett 2010; 195
- 14 Obaid-Ur-Rahman A, Ibad MF, Nawaz M, Adeel M, Rama NH, Villinger A, Langer P. Tetrahedron Lett. 2010; 51: 657
- 15 Obaid-Ur-Rahman A, Ibad MF, Nawaz M, Ali A, Sher M, Rama NH, Villinger A, Langer P. Tetrahedron Lett. 2010; 51: 1541
- 16 Ibad MF, Eleya N, Obaid-Ur-Rahman A, Mahal A, Hussain M, Villinger A, Langer P. Synthesis 2011; 2101
- 17a Khera RA, Nawaz M, Feist H, Villinger A, Langer P. Synthesis 2012; 44: 219
- 17b Nawaz M, Khera RA, Malik I, Ibad MF, Abid OU. R, Villinger A, Langer P. Synlett 2010; 979
- 18 Nawaz M, Ullah I, Obaid-Ur-Rahman A, Villinger A, Langer P. Eur. J. Org. Chem. 2011; 6670
- 19 Nawaz M, Adeel M, Ibad MF, Langer P. Synlett 2009; 2154
- 20a Ali A, Khera RA, Ibad MF, Hussain M, Langer P. Synlett. 2010; 731
- 20b Khera RA, Ali A, Hussain M, Ibad MF, Villinger A, Langer P. ChemCatChem 2012; 4: 356
- 21 Akrawi OA, Mohammed HM, Patonay T, Villinger A, Langer P. Tetrahedron 2012; 68: 6298
- 22 Zinad DS, Hussain M, Akrawi OA, Villinger A, Langer P. Tetrahedron Lett. 2011; 52: 3451
- 23 Zinad DS, Feist H, Villinger A, Langer P. Tetrahedron 2012; 68: 711
- 24 Malik I, Hussain M, Hung NT, Villinger A, Langer P. Synlett 2010; 2244
- 25 Eleya N, Malik I, Reimann S, Wittler K, Hein M, Patonay T, Villinger A, Ludwig R, Langer P. Eur. J. Org. Chem. 2012; 1639
- 26 Eleya N, Khaddour Z, Patonay T, Langer P. Synlett 2012; 23: 223
- 27a Mahal A, Villinger A, Langer P. Synlett 2010; 1085
- 27b Mahal A, Villinger A, Langer P. Eur. J. Org. Chem. 2011; 2075
- 28 Akrawi OA, Hussain M, Langer P. Tetrahedron Lett. 2011; 52: 1093
- 29 Salman GA, Mahal A, Shkoor M, Hussain M, Villinger A, Langer P. Tetrahedron Lett. 2011; 52: 392
- 30 Salman GA, Hussain M, Villinger A, Langer P. Synlett 2010; 3031
For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:
For a simple guide for predicting the site selectivity of palladium-catalyzed cross-coupling reactions based on 1H NMR spectroscopic data of the nonhalogenated derivatives, see: