18 F. Schneider and B. Ondruschka, ChemSusChem, 2008, 1, 622–625.
19 L. M. Klingensmith and N. E. Leadbeater, Tetrahedron Lett., 2003, 44,
765–768.
2 mL; the reaction solutions were dried (MgSO4) and analyzed
by GC-FID and GC-MS.
20 E. Tullberg, D. Peters and T. Frejd, J. Organomet. Chem., 2004, 689,
3778–3781.
21 D. A. Fulmer, W. C. Shearhouse, S. T. Mendonza and J. Mack, Green
Chem., 2009, 11, 1821–1825.
General reaction procedure (method C)
The milling beakers were filled with milling balls and then
milling auxiliary (4 g), CuBr2 (1.5 mmol, 335 mg), and phenyl-
boronic acid (1.5 mmol, 183 mg) were added sequentially.
Milling was performed at specific oscillation frequency and
milling time. After cooling to room temperature, the crude pro-
ducts were extracted on a frit with a thin silica layer by using
MTBE (3 × 15 mL). The solvent was evaporated in vacuum to a
volume of 2 mL; the reaction solutions were dried (MgSO4) and
analyzed by GC-FID and GC-MS.
22 R. Thorwirth, A. Stolle and B. Ondruschka, Green Chem., 2010, 12,
985–991.
23 N. N. Karade, G. B. Tiwari, D. B. Huple and T. A. J. Siddiqui, J. Chem.
Res., 2006, 2006, 366–368.
24 V. Kavala, S. Naik and B. K. Patel, J. Org. Chem., 2005, 70, 4267–
4271.
25 H. Sohmiya, T. Kimura, M. Fujita and T. Ando, Tetrahedron, 1998, 54,
13737–13750.
26 J. A. R. P. Sarma and A. Nagaraju, J. Chem. Soc., Perkin Trans. 2, 2000,
1113–1118.
27 G. K. Imanzadeh, M. R. Zamanloo, H. Eskandari and K. Shayesteh,
J. Chem. Res., 2006, 2006, 151–153.
28 A. N. M. M. Rahman, R. Bishop, R. Tan and N. Shan, Green Chem.,
2005, 7, 207–209.
29 F. Schneider, T. Szuppa, A. Stolle, B. Ondruschka and H. Hopf, Green
Chem., 2009, 11, 1894–1899.
30 M. Eissen, M. Strudthoff, S. Backhaus, C. Eismann and G. Oetken,
J. Chem. Educ., 2011, 88, 284–291.
Acknowledgements
This work was partially funded by the German Federal Environ-
mental Foundation (DBU; grant no. 27281-31).
31 R. Thorwirth, F. Bernhardt, A. Stolle, B. Ondruschka and J. Asghari,
Chem.–Eur. J., 2010, 16, 13236–13242.
32 J. Gao and G.-W. Wang, J. Org. Chem., 2008, 73, 2955–2958.
33 S. M. Hick, C. Griebl, D. T. Restrepo, J. H. Truitt, E. J. Buker, C. Bylda
and R. G. Blair, Green Chem., 2010, 12, 468–474.
34 G. Lente, J. Kalmár, Z. Baranyai, A. Kun, I. Kék, D. Bajusz, M. Takács,
L. Veres and I. Fábián, Inorg. Chem., 2009, 48, 1763–1773.
35 H. L. Polak, G. Feenstra and J. Slagman, Talanta, 1966, 13, 715–
724.
Notes and references
1 K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025–1074.
2 K. Tanaka, Solvent-free Organic Synthesis, Wiley-VCH, Weinheim, 2nd
edn, 2008.
3 Z. V. Todres, Organic Mechanochemistry and its Practical Applications,
Taylor & Francis, Boca Raton, 2006.
36 C. E. S. Cortes and R. B. Faria, Inorg. Chem., 2004, 43, 1395–1402.
37 Z. Zhang, Y.-W. Dong, G.-W. Wang and K. Komatsu, Synlett, 2004,
61–64.
38 F. Schneider, A. Stolle, B. Ondruschka and H. Hopf, Org. Process Res.
Dev., 2009, 13, 44–48.
4 B. Rodríguez, A. Bruckmann, T. Rantanen and C. Bolm, Adv. Synth.
Catal., 2007, 349, 2213–2233.
5 A. Stolle, T. Szuppa, S. E. S. Leonhardt and B. Ondruschka, Chem. Soc.
Rev., 2011, 40, 2317–2329.
6 G.-W. Wang, in Encyclopedia of Nanoscience and Nanotechnology, ed.
H. S. Nalwa, American Scientific Publishers, Stevenson Ranch, 2003,
vol. 3, pp. 557–565.
39 E. M. C. Gérad, H. Sahin, A. Encinas and S. Bräse, Synlett, 2008, 7202–
7204.
40 T. Friščić and L. Fábián, CrystEngComm, 2009, 11, 743–745.
41 G. A. Bowmaker, N. Chaichit, C. Pakawatchai, B. W. Skelton and
A. H. White, Dalton Trans., 2008, 2926–2928.
42 G. A. Bowmaker, J. V. Hanna, R. D. hart, B. W. Skelton and
A. H. White, Dalton Trans., 2008, 5290–5292.
7 B. Rodríguez, A. Bruckmann and C. Bolm, Chem.–Eur. J., 2007, 13,
4710–4722.
8 J. G. Hernández and E. Juaristi, Tetrahedron, 2011, 67, 6953–6959.
9 G. Kaupp, M. R. Naimi-Jamal and J. Schmeyers, Tetrahedron, 2003, 59,
3753–3760.
43 M. Nüchter, R. Trotzki and B. Ondruschka, J. Prakt. Chem., 2000, 342,
720–724.
10 A. Baron, J. Martinez and F. Lamaty, Tetrahedron Lett., 2010, 51, 6246–
6249.
44 T. Friščić, A. V. Trask, W. Jones and W. D. S. Motherwell, Angew. Chem.,
11 M. A. P. Martins, C. P. Frizzo, D. N. Moreira, L. Buriol and P. Machado,
Chem. Rev., 2009, 109, 4140–4182.
Int. Ed., 2006, 45, 7546–7550.
45 K.-J. Lee, H. K. Cho and C.-E. Song, Bull. Korean Chem. Soc., 2002,
23, 773–775.
12 R. Thorwirth, A. Stolle, B. Ondruschka, A. Wild and U. S. Schubert,
Chem. Commun., 2011, 47, 4370–4372.
46 B. Priewisch and K. R. Braun, J. Org. Chem., 2005, 70, 2350–2352.
47 Z. Bodnar, T. Mallat and A. Baiker, J. Mol. Catal. A: Chem., 1996, 110,
55–63.
48 Y. Li, W. Liu, M. Wu, Z. Yi and J. Zhang, J. Mol. Catal. A: Chem., 2007,
261, 73–78.
49 T. Miyazaki, S. Munemiya and A. Tasaka, US3932475, 1976.
50 M. Eissen and D. Lenoir, Chem.–Eur. J., 2008, 14, 9830–9841.
51 C. Ye and J. M. Shreeve, J. Org. Chem., 2004, 69, 8561–8563.
52 J. M. Murphy, X. Liao and J. F. Hartwig, J. Am. Chem. Soc., 2007, 129,
15434–15435.
13 T. Szuppa, A. Stolle, B. Ondruschka and W. Hopfe, Green Chem., 2010,
12, 1288–1294.
14 T. Szuppa, A. Stolle, B. Ondruschka and W. Hopfe, ChemSusChem,
2010, 3, 1181–1191.
15 J. Mack, D. Fulmer, S. Sofel and N. Santos, Green Chem., 2007, 9,
1041–1043.
16 R. Schmidt, R. Thorwirth, T. Szuppa, A. Stolle, B. Ondruschka and
H. Hopf, Chem.–Eur. J., 2011, 17, 8129–8138.
17 S. Feldbaek-Nielsen, D. Peters and O. Axelsson, Synth. Commun., 2000,
30, 3501–3509.
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