Dimerization of Aryl Sulfonates by in situ Generated Nickel(0)

Jacques Maddaluno; Muriel Durandetti

doi:10.1055/s-0035-1560712

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(17): 2385-2388
DOI: 10.1055/s-0035-1560712

cluster

Dimerization of Aryl Sulfonates by in situ Generated Nickel(0)

Jacques Maddaluno

Laboratoire COBRA – CNRS UMR 6014 & FR 3038, Université de Rouen INSA de Rouen, 76821 Mt St Aignan Cedex, France eMail: muriel.durandetti@univ-rouen.fr

,

Muriel Durandetti*

Laboratoire COBRA – CNRS UMR 6014 & FR 3038, Université de Rouen INSA de Rouen, 76821 Mt St Aignan Cedex, France eMail: muriel.durandetti@univ-rouen.fr

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

This paper is dedicated to the memory of Professor Manfred Schlosser.

Abstract

A mild and user-friendly nickel-catalyzed method for the reductive homocoupling of aromatic tosylates is presented. The reaction proceeds between room temperature and 60 °C, with stable substrates (ArOTs) easily prepared from inexpensive and commercially available phenols or naphthols. It relies on a catalytic amount (10 mol%) of a robust catalyst (NiBr₂bipy) that does not require the preparation of sensitive organometallic intermediates. Yields are good to excellent.

Key words

aryl tosylates - biaryls - dimerization - nickel catalysis - Ullmann-type reaction

Volltext

Referenzen

References and Notes

1a Schlosser M. J. Organomet. Chem. 1967; 8: 9
1b Schlosser M, Desponds O, Lehmann R, Moret E, Rauchschwalbe G. Tetrahedron 1993; 49: 10175
1c Schlosser M In Organometallics in Synthesis: A Manual . Schlosser M. Wiley; London: 1994
1d Schlosser M In Organometallics in Synthesis: A Manual . 2nd ed., Schlosser M. Wiley; Chichester: 2002
1e Schlosser M. Angew. Chem Int. Ed. 2005; 44: 376
1f Cottet F, Castagnetti E, Schlosser M. Synthesis 2005; 798
1g Schlosser M, Mangano G, Leroux F. Eur. J. Org. Chem. 2005; 5049
1h Ruzziconi R, Spizzichino S, Giurg M, Castagnetti E, Schlosser M. Synthesis 2010; 1531

2a Ruzziconi R, Spizzichino S, Mazzanti A, Lunazzi L, Schlosser M. Org. Biomol. Chem. 2010; 8: 4463
2b Mazzanti A, Lunazzi L, Ruzziconi R, Spizzichino S, Schlosser M. Chem. Eur. J. 2010; 16: 9186
2c Lunazzi L, Mancinelli M, Mazzanti A, Lepri S, Ruzziconi R, Schlosser M. Org. Biomol. Chem. 2012; 10: 1847

3a Wu X.-F, Anbrasan P, Neumann H, Beller M. Angew. Chem. Int. Ed. 2010; 49: 9047
3b Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

4a Jolly PW, Willic G In The Organic Chemistry of Nickel . Vol. 1 and 2. Academic Press; New York: 1974
4b Ikeda S.-i In Modern Organonickel Chemistry . Tamaru Y. Wiley-VCH; Weinheim: 2005
4c Hachiya H, Hirano K, Satoh T, Miura M. ChemCatChem 2010; 2: 1403
4d Hachiya H, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2010; 49: 2202
4e Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 5743

5a Durandetti M, Nédélec J.-Y, Périchon J. J. Org. Chem. 1996; 61: 1748
5b de França KW. R, Navarro M, Léonel E, Durandetti M, Nédélec JY. J. Org. Chem. 2002; 67: 1838
5c Durandetti M, Périchon J. Synthesis 2004; 3079
5d Durandetti M, Gosmini C, Périchon J. Tetrahedron 2007; 63: 1146
5e Gosmini C, Bassene-Ernst C, Durandetti M. Tetrahedron 2009; 65: 6141
5f Durandetti M, Hardou L, Clément M, Maddaluno J. Chem. Commun. 2009; 4753
5g Durandetti M, Hardou L, Lhermet R, Rouen M, Maddaluno J. Chem. Eur. J. 2011; 17: 12773

6a Jutand A, Mosleh A. J. Org. Chem. 1997; 62: 261
6b Huang X, Anderson KW, Zim D, Jiang L, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 6653
6c Wilson DA, Wilson CJ, Rosen BM, Percec V. Org. Lett. 2008; 10: 4879
6d Liao X, Weng Z, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 195
6e Gooßen LJ, Rodríguez N, Lange PP, Linder C. Angew. Chem. Int. Ed. 2010; 49: 1111

7a Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
7b Tang Z.-Y, Hu Q.-S. J. Am. Chem. Soc. 2004; 126: 3058
7c Gao C.-Y, Yang L.-M. J. Org. Chem. 2008; 73: 1624
7d Kim C.-B, Jo H, Ahn B.-K, Kim CK, Park K. J. Org. Chem. 2009; 74: 9566
7e Wilson DA, Wilson CJ, Moldoveanu C, Resmerita A.-M, Corcoran P, Hoang LM, Rosen BM, Percec V. J. Am. Chem. Soc. 2010; 132: 1800
7f Mesganaw T, Garg NK. Org. Process Res. 2013; 17: 29
7g Jerozek RL, Zhang N, Leowanawat P, Bunner MH, Gutsche N, Pesti AK. R, Olsen JT, Percec V. Org. Lett. 2014; 16: 6326
7h Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346

8a Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
8b Yamaguchi J, Muto K, Itami K. Eur. J. Org. Chem. 2013; 19

9 Bringmann G, Walter R, Weirich R. Angew. Chem., Int. Ed. Engl. 1990; 29: 977
10 Ullmann F, Bielecki J. Ber. Dtsch. Chem. Ges. 1901; 2174

11a Kuroboshi M, Waki Y, Tanaka H. J. Org. Chem. 2003; 68: 3938
11b Nising CF, Schmid UK, Nieger M, Bräse S. J. Org. Chem. 2004; 69: 6830
11c Amatore C, Cammoun C, Jutand A. Eur. J. Org. Chem. 2008; 4567
11d Robo MT, Prinsell MR, Weix DJ. J. Org. Chem. 2014; 79: 10624

12a Semmelhack MF, Helquist PM, Jones LD. J. Am. Chem. Soc. 1971; 93: 5908
12b Kende AS, Liebeskind LS, Braitsch DM. Tetrahedron Lett. 1975; 16: 3375
12c Lourak M, Vanderesse R, Fort Y, Caubère P. J. Org. Chem. 1989; 54: 4840
12d Iyoda M, Otsuka H, Sato K, Nisato N, Oda M. Bull. Chem. Soc. Jpn. 1990; 63: 80
12e Percec V, Bae J.-Y, Zhao M, Hill DH. J. Org. Chem. 1995; 60: 176
12f Hong R, Hoen R, Zhang J, Lin G.-Q. Synlett 2001; 1527

13a Troupel M, Rollin Y, Sibille S, Périchon J. J. Organomet. Chem. 1980; 202: 435
13b Rollin Y, Troupel M, Tuck DG, Périchon J. J. Organomet. Chem. 1986; 303: 131
13c Meyer G, Rollin Y, Périchon J. J. Organomet. Chem. 1987; 333: 263

14 Amatore C, Jutand A. J. Electroanal. Chem. 1991; 306: 125

15a Durandetti M, Devaud M, Périchon J. New J. Chem. 1996; 20: 659
15b Jiang F, Ren Q. J. Organomet. Chem. 2014; 757: 72

16a Buonomo JA, Everson DA, Weix DJ. Synthesis 2013; 3099
16b Liao L.-Y, Kong X.-R, Duan X.-F. J. Org. Chem. 2014; 79: 777

17 Representative Procedure for the Nickel-Catalyzed Formation of BiarylsTo a solution of aryl tosylate (2 mmol, 1 equiv) in anhydrous DMF (5 mL) under an argon atmosphere at room temperature (or 60 °C for o-substituted or electron-donating substituents) was added manganese (4 mmol, 2 equiv) followed by NiBr₂bipy (0.2 mmol, 0.1 equiv), then rapidly TFA (10 μL). The medium was vigorously stirred, and the disappearance of starting material was monitored by gas chromatography. The reaction was stopped after the aryl tosylate was consumed (ca. 1 h). The mixture was hydrolyzed with HCl 1 M (5 mL) and diluted with Et₂O (15 mL). The aqueous layer was extracted with Et₂O (2 × 15 mL), then combined organic layers were washed with water (2 × 15 mL) and brine (15 mL), dried over anhydrous MgSO₄, and concentrated. The crude was purified by recrystallization.1,1′-Biphenyl¹⁸ (CAS registry number: 92-52-4)The pure product is isolated in 91% as white crystals; mp 68 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.35 (t, J = 7.4 Hz, 2 H), 7.4 (t, J = 7.7 Hz, 4 H), 7.59 (d, J = 7.8 Hz, 4 H) ppm. ¹³C NMR (75 MHz, CDCl₃): δ = 127.3 (2 C), 127.4, 128.9 (2 C), 141.4 ppm. MS (EI, 70 eV): m/z = 154 [M⁺], 77 [M/2, base].
18 Cahiez G, Chaboche C, Mahuteau-Betzer F, Ahr M. Org. Lett. 2005; 7: 1943

Zusatzmaterial

Supporting Information