8 of 8
KEESARA ET AL.
[5] L. Pu, Acc. Chem. Res. 2012, 45, 150.
[14] a) D. Morales‐Morales, Rev. Soc. Quím. Méx. 2004, 48, 338; b)
N. Selander, K. J. Szabó, Chem. Rev. 2011, 111, 2048; c) C.
Gunanathan, D. Milstein, Chem. Rev. 2014, 114, 12024; d) M. E.
O’Reilly, A. S. Veige, Chem. Soc. Rev. 2014, 43, 6325; e) H. A.
Younus, W. Su, N. Ahmad, S. Chen, F. Verpoort, Adv. Synth. Catal.
2015, 357, 283; f) K. J. Szabó, O. F. Wendt (Eds), Pincer and
Pincer‐Type Complexes: Applications in Organic Synthesis and
Catalysis, Wiley‐VCH, Weinheim 2014.
[6] a) S. T. Wu, D. K. Yang, Reflective Liquid Crystal Displays, Wiley,
New York 2001; b) Y.‐L. Wu, F. Ferroni, S. Pieraccini, W. B.
Schweizer, B. B. Frank, G. P. Spada, F. Diederich, Org. Biomol.
Chem. 2012, 10, 8016.
[7] a) J. Zhao, Y. Wang, Y. He, L. Liu, Q. Zhu, Org. Lett. 2012, 14,
1078; b) Q. Shou, L. K. Banbury, D. E. Renshaw, E. H. Lambley,
H. Mon, G. A. Macfarlane, H. J. Griesser, M. M. Heinrich, H.
Wohlmuth, J. Nat. Prod. 2012, 75, 1612; c) M. Millot, A. Dieu,
S. Tomasi, Nat. Prod. Rep. 2016, 33, 801.
[15] D. D. Perrin, W. L. F. Armarego, D. P. Perrin, Purification of
Laboratory Chemicals, 2nd ed., Pergamon, Oxford 1983.
[16] CrysAlisPro, Agilent Technologies, Yarnton, UK, 2014.
[17] S. Parkin, B. Moezzi, H. Hope, J. Appl. Crystallogr. 1995, 28, 53.
[18] G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
[19] L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, 849.
[8] a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; b) S. Kotha,
K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633; c) G. A.
Molander, B. Canturk, Angew. Chem. Int. Ed. 2009, 48, 9240; d)
A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6722; e) F.‐S. Han,
Chem. Soc. Rev. 2013, 42, 5270; f) A. J. J. Lennox, G. C. Lloyd‐
Jones, Chem. Soc. Rev. 2014, 43, 412; g) S. Paul, M. M. Islam,
S. M. Islam, RSC Adv. 2015, 5, 42193; h) I. Maluenda, O. Navarro,
Molecules 2015, 20, 7528; i) P. Das, W. Linert, Coord. Chem. Rev.
2016, 311, 1.
[20] C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P.
McCabe, E. Pidcock, L. Rodriguez‐Monge, R. Taylor, J. van de
Streek, P. A. Wood, J. Appl. Crystallogr. 2008, 41, 466.
[21] a) Y.‐S. Uh, H. Zhang, C. M. Vogels, A. Decken, S. A. Westcott,
Bull. Korean Chem. Soc. 2004, 25, 986; b) H.‐F. Guo, X. Zhao,
D.‐Y. Ma, A.‐P. Xie, W.‐B. Shen, Transition Met. Chem. 2013,
38, 299; c) A. Akbari, M. Ahmadi, R. Takjoo, F. W. Heinemann,
J. Coord. Chem. 2013, 66, 1866; d) L. A. Wright, E. G. Hope,
G. A. Solan, W. B. Crossa, K. Singh, Dalton Trans. 2015, 44,
6040; e) J.‐J. Yan, C.‐G. Zheng, Acta Crystallogr. 2015, E71, m124.
[9] a) J. J. Molloy, R. P. Law, J. W. B. Fyfe, C. P. Seath, D. J. Hirst,
A. J. B. Watson, Org. Biomol. Chem. 2015, 13, 3093; b) J. D. Revell,
A. Ganesan, Org. Lett. 2002, 4, 3071.
[10] a) P. Wawrzyniak, J. Heinicke, Tetrahedron Lett. 2006, 47, 8921; b)
W. Y. Wu, S. N. Chen, F. Y. Tsai, Tetrahedron Lett. 2006, 47, 9267;
c) S. Liu, M. Lv, D. Xiao, X. Li, X. Zhou, M. Guo, Org. Biomol.
Chem. 2014, 12, 4511.
[22] A. Akbari, Z. Alinia, Turk. J. Chem. 2013, 37, 867.
[23] K. Nakamoto, Infrared and Raman Spectra of Inorganic and
Coordination Compounds, 4th ed., Wiley, New York 1986, 233.
[11] a) B. Schmidt, M. Riemer, J. Org. Chem. 2014, 79, 4104; b) B.
Schmidt, M. Riemer, M. Karras, J. Org. Chem. 2013, 78, 8680;
c) H. Sakurai, T. Tsukuda, T. Hirao, J. Org. Chem. 2002, 67,
2721; d) N. Iranpoor, H. Firouzabadi, A. Safavi, S. Motevalli,
M. M. Doroodmand, Appl. Organomet. Chem. 2012, 26, 417;
e) G. M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth,
R. Mulhaupt, J. Am. Chem. Soc. 2009, 131, 8262; f) P. P. Zhang,
X. X. Zhang, H. X. Sun, R. H. Liu, B. Wang, Y. H. Lin, Tetrahedron
Lett. 2009, 50, 4455; g) G. Wei, W. Zhang, F. Wen, Y. Wang,
M. Zhang, J. Phys. Chem. C 2008, 112, 10827; h) G. Durgun,
O. Aksın, L. Artok, J. Mol. Catal. A 2007, 278, 189; i) K. Srinivas,
M. M. Rao, P. Saiprathima, Appl. Catal. A 2015, 496, 58.
[24] I. P. Beletskaya, A. V. Cheprakov, in Handbook of
Organopalladium Chemistry for Organic Synthesis, (Ed: E. Negishi),
Wiley, New York 2003, 2960.
[25] Q. Li, L.‐M. Zhang, J.‐J. Bao, H.‐X. Li, J.‐B. Xie, J.‐P. Lang, Appl.
Organomet. Chem. 2014, 28, 861.
SUPPORTING INFORMATION
CCDC 1518767 contains the supplementary crystallographic
data for [Pd(L)(OAc)]. These data can be obtained free of
or from the Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: (+44)1223‐
336‐033; or e‐mail: deposit@ccdc.cam.ac.uk.
[12] a) D.‐X. Liu, W.‐J. Gong, H.‐X. Li, J. Gao, F.‐L. Li, J.‐P. Lang,
Tetrahedron 2014, 70, 3385; b) G. Zhang, W. Zhang, Y. Luan, X.
Han, C. Ding, Chin. J. Chem. 2015, 33, 705; c) J.‐J. Ning, J.‐F.
Wang, Z.‐G. Ren, D. J. Young, J.‐P. Lang, Tetrahedron 2015, 71,
4000; d) A. Chatterjee, T. R. Ward, Catal. Lett. 2016, 146, 820.
[13] a) T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem. 2005,
70, 2191; b) I. D. Kostas, B. R. Steele, A. Terzis, S. V. Amosova, A.
V. Martynov, N. A. Makhaeva, Eur. J. Inorg. Chem. 2006, 2642;
c) P. R. Kumar, S. Upreti, A. K. Singh, Polyhedron 2008, 27,
1610; d) A. Kumar, M. Agarwal, A. K. Singh, J. Organometal.
Chem. 2008, 693, 3533; e) A. Kumar, M. Agarwal, A. K. Singh,
R. J. Butcher, Inorg. Chim. Acta 2009, 362, 3208; f) Z. Zhou, Z.
Zhou, A. Chen, X. Zhou, Q. Qi, Y. Xie, Transition Met. Chem.
2013, 38, 401; g) P. Pattanayak, D. Patra, P. Brandao, D.
Mal, V. Felix, Inorg. Chem. Commun. 2015, 53, 68.
How to cite this article: Keesara S, Narendra Babu
G, Pal S. An acetatopalladium(II) complex with 1‐
benzyl‐N‐(3,5‐di‐tert‐butylsalicylidene)piperidin‐4‐
amine: Synthesis, structure and catalytic applications
in Suzuki–Miyaura coupling of arylboronic acids with
hydroxyaryl halides. Appl Organometal Chem.