Job/Unit: O42134
/KAP1
Date: 29-04-14 18:19:06
Pages: 7
Palladium and TEMPO as Co-Catalysts in Homocoupling
[18] H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron
Lett. 2003, 44, 1541–1544.
[19] K. Xie, S. Wang, Z. Yang, J. Liu, A. Wang, X. Li, Z. Tan, C.-
C. Guo, W. Deng, Eur. J. Org. Chem. 2011, 5787–5790.
[20] J. Cornella, H. Lahlali, I. Larrosa, Chem. Commun. 2010, 46,
8276–8278.
(NMR, GC–MS) matched those reported in the literature for 4,4Ј-
dichloro-1,1Ј-biphenyl 6g.[63] 1H NMR (500 MHz, CDCl3): δ =
7.40 (m, 4 H), 7.47 (m, 4 H) ppm. 13C NMR (75 MHz, CDCl3): δ
= 128.2, 129.0, 133.7, 138.4 ppm. MS (EI, 70 eV): m/z (%) = 152.1
(90), 224.1 (100) [M]+.
[21] L. O. Sraj, G. N. Khairallah, G. da Silva, R. A. J. O’Hair, Orga-
nometallics 2012, 31, 1801–1807.
[22] L. E. Apodaca, U. S. Geol. Surv., Mineral Commodity Summar-
ies, 2013.
[23] F. Pan, Z.-J. Shi, ACS Catal. 2014, 4, 280–288.
[24] L. Wang, W. He, Z. Yu, Chem. Soc. Rev. 2013, 42, 599–621.
[25] S. R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 2005, 44, 7674–
7684; Angew. Chem. 2005, 117, 7848–7859.
[26] K. Garves, J. Org. Chem. 1970, 35, 3273–3275.
[27] R. Selke, W. Thiele, J. Prakt. Chem. 1971, 313, 875–881.
[28] K. Bal Raju, V. Mari, K. Nagaiah, Synthesis 2013, 45, 2867–
2874.
4,4Ј-Difluoro-1,1Ј-biphenyl 6h [CAS Reg. No.: 398-23-2]: Com-
pound 6h was prepared from sodium 4-fluorobenzenesulfinate 4h
(91 mg, 0.5 mmol). Purification by column chromatography with
hexanes gave a colorless solid (32 mg, 0.17 mmol, 67%, procedure
A; 14 mg, 0.07 mmol, 29%, procedure B). The spectroscopic data
(NMR, GC–MS) matched those reported in the literature for 4,4Ј-
difluoro-1,1Ј-biphenyl 6h.[63] 1H NMR (500 MHz, CDCl3): δ = 7.11
(m, 4 H), 7.48 (m, 4 H) ppm. 13C NMR (125 MHz, CDCl3): δ =
2
3
1
115.7 (d, J = 21.5 Hz), 128.6 (d, J = 9 Hz), 136.4, 162.4 (d, J =
245 Hz) ppm. MS (EI, 70 eV): m/z (%) = 190.1 (100) [M]+.
Supporting Information (see footnote on the first page of this arti-
cle): Copies of the 1H NMR and 13C NMR spectra are available
for all products.
[29] S. Hu, P. Xia, K. Cheng, C. Qi, Appl. Organomet. Chem. 2013,
27, 188–190.
[30] N. Taniguchi, Synlett 2013, 24, 2571–2574.
[31] G.-W. Wang, T. Miao, Chem. Eur. J. 2011, 17, 5787–5790.
[32] X. Zhou, J. Luo, J. Liu, S. Peng, G.-J. Deng, Org. Lett. 2011,
13, 1432–1435.
[33] S. Liu, Y. Bai, X. Cao, F. Xiao, G.-J. Deng, Chem. Commun.
2013, 49, 7501–7503.
Acknowledgments
[34] H. Wang, Y. Li, R. Zhang, K. Jin, D. Zhao, C. Duan, J. Org.
Chem. 2012, 77, 4849–4853.
[35] W. Chen, X. Zhou, F. Xiao, J. Luo, G.-J. Deng, Tetrahedron
Lett. 2012, 53, 4347–4350.
[36] M. Behrends, J. Sävmarker, P. J. R. Sjöberg, M. Larhed, ACS
Catal. 2011, 1, 1455–1459.
[37] T. Miao, G.-W. Wang, Chem. Commun. 2011, 47, 9501–9503.
[38] H. Rao, L. Yang, Q. Shuai, C.-J. Li, Adv. Synth. Catal. 2011,
353, 1701–1706.
This work was funded by the Natural Sciences and Engineering
Research Council of Canada (NSERC) and Le Fonds de Recherche
du Québec, Nature et Technologies (FQRNT). Support was also
kindly provided by Boehringer Ingelheim, Wyeth, Merck Frosst,
and Concordia University. The authors thank Professor Shawn
Collins (Université de Montréal) and Simon Woo (Concordia Uni-
versity) for helpful discussions of the manuscript. Dirk Ortgies is
grateful to the Centre in Green Chemistry and Catalysis and Con-
cordia University for scholarships.
[39] J. Liu, X. Zhou, H. Rao, F. Xiao, C.-J. Li, G.-J. Deng, Chem.
Eur. J. 2011, 17, 7996–7999.
[40] T. Miao, L. Wang, Adv. Synth. Catal. 2014, 356, 429–436.
[41] M. Wang, D. Li, W. Zhou, L. Wang, Tetrahedron 2012, 68,
1926–1930.
[1] P. J. Hajduk, M. Bures, J. Praestgaard, S. W. Fesik, J. Med.
Chem. 2000, 43, 3443–3447.
[2] A. P. Degnan, A. I. Meyers, J. Am. Chem. Soc. 1999, 121,
[42] B. Liu, J. Li, F. Song, J. You, Chem. Eur. J. 2012, 18, 10830–
2762–2769.
10833.
[3] L. Pu, Chem. Rev. 1998, 98, 2405–2494.
[4] L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int.
Ed. 2009, 48, 9792–9826; Angew. Chem. 2009, 121, 9976–10011.
[5] F. Ullmann, J. Bielecki, Ber. Dtsch. Chem. Ges. 1901, 34, 2174–
2185.
[43] J. Chen, Y. Sun, B. Liu, D. Liu, J. Cheng, Chem. Commun.
2012, 48, 449–451.
[44] C. Zhou, Y. Li, Y. Lu, R. Zhang, K. Jin, X. Fu, C. Duan, Chin.
J. Chem. 2013, 31, 1269–1273.
[45] J. Colomb, T. Billard, Tetrahedron Lett. 2013, 54, 1471–1474.
[46] F. Zhao, Q. Tan, F. Xiao, S. Zhang, G.-J. Deng, Org. Lett.
2013, 15, 1520–1523.
[47] W. Chen, P. Li, T. Miao, L.-G. Meng, L. Wang, Org. Biomol.
Chem. 2012, 11, 420–424.
[48] C. Zhou, Q. Liu, Y. Li, R. Zhang, X. Fu, C. Duan, J. Org.
Chem. 2012, 77, 10468–10472.
[49] K. Sato, T. Okoshi, Process For Producing Aromatic Com-
pound, 1992, US Patent 5,159,082.
[50] M. Wu, J. Luo, F. Xiao, S. Zhang, G.-J. Deng, H.-A. Luo, Adv.
Synth. Catal. 2012, 354, 335–340.
[51] R. Chen, S. Liu, X. Liu, L. Yang, G.-J. Deng, Org. Biomol.
Chem. 2011, 9, 7675–7679.
[6] J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire,
Chem. Rev. 2002, 102, 1359–1470.
[7] R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461–
1473.
[8] C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V.
Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062–5085; Angew.
Chem. 2012, 124, 5150–5174.
[9] T. Newhouse, P. S. Baran, Angew. Chem. Int. Ed. 2011, 50,
3362–3374; Angew. Chem. 2011, 123, 3422–3435.
[10] W. I. Dzik, P. P. Lange, L. J. Gooßen, Chem. Sci. 2012, 3, 2671–
2678.
[11] N. Rodríguez, L. J. Gooßen, Chem. Soc. Rev. 2011, 40, 5030–
5048.
[52] B. Rao, W. Zhang, L. Hu, M. Luo, Green Chem. 2012, 14,
[12] T. Satoh, M. Miura, Synthesis 2010, 3395–3409.
[13] G. Cheng, M. Luo, Eur. J. Org. Chem. 2011, 2519–2523.
[14] M. S. Maji, T. Pfeifer, A. Studer, Angew. Chem. Int. Ed. 2008,
47, 9547–9550; Angew. Chem. 2008, 120, 9690–9692.
[15] Y. Yamamoto, Synlett 2007, 1913–1916.
[16] H. Sakurai, H. Tsunoyama, T. Tsukuda, J. Organomet. Chem.
2007, 692, 368–374.
3436.
[53] S. Sévigny, P. Forgione, New J. Chem. 2013, 37, 589.
[54] S. Sévigny, P. Forgione, Chem. Eur. J. 2013, 19, 2256–2260.
[55] D. Ortgies, P. Forgione, Synlett 2013, 24, 1715–1721.
[56] D. Ortgies, A. Barthelme, S. Aly, B. Desharnais, S. Rioux, P.
Forgione, Synthesis 2013, 45, 694–702.
[57] T. Vogler, A. Studer, Synthesis 2008, 1979–1993.
[58] R. Ciriminna, M. Pagliaro, Org. Process Res. Dev. 2010, 14,
245–251.
[17] T. D. Nelson, R. D. Crouch, Cu, Ni, and Pd Mediated Homo-
coupling Reactions in Biaryl Syntheses: The Ullmann Reaction.
Organic Reactions, John Wiley & Sons, Hoboken, NJ, USA,
2004.
[59] T. Vogler, A. Studer, Adv. Synth. Catal. 2008, 350, 1963–1967.
Eur. J. Org. Chem. 0000, 0–0
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
5