Regioselective Suzuki–Miyaura Reactions of Aromatic Bis-triflates: Electronic versus Steric Effects

Zahid Hassan; Tamás Patonay; Peter Langer

doi:10.1055/s-0032-1317944

Synlett, Table of Contents

Synlett 2013; 24(4): 412-423
DOI: 10.1055/s-0032-1317944

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Regioselective Suzuki–Miyaura Reactions of Aromatic Bis-triflates: Electronic versus Steric Effects

Zahid Hassan

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Fax: +49(381)4986412 Email: zhassanhej@yahoo.com Email: peter.langer@uni-rostock.de

^bLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

,

Tamás Patonay

^cDepartment of Organic Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary

,

Peter Langer*

^aInstitut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany Fax: +49(381)4986412 Email: zhassanhej@yahoo.com Email: peter.langer@uni-rostock.de

^bLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

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Abstract

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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

Key words

palladium - catalysis - regioselectivity - Suzuki–Miyaura reaction - bis-triflates

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References

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

For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:

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.

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:

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