Synthesis of N-Arylamides by Copper-Catalyzed Amination of Aryl Halides
2
011, 40, 3405–3415; c) D.-W. Zhang, X. Zhao, J.-L.
Kaden, Dalton Trans. 2005, 30–36; d) S. Sahnoun, S.
Messaoudi, J.-F. Peyrat, J.-D. Brion, M. Alami, Tetrahe-
dron Lett. 2012, 53, 2860–2863; e) Z. Li, L. Wang, X.
Zhou, Adv. Synth. Catal. 2012, 354, 584–588; f) T.
Hirano, K. Uehara, K. Kamata, N. Mizuno, J. Am.
Chem. Soc. 2012, 134, 6425–6433.
Hou, Z.-T. Li, Chem. Rev. 2012, 112, 5271–5316; d) R.
Garcꢂa-ꢃlvarez, P. Crochet, V. Cadierno, Green Chem.
2
013, 15, 46–66.
2] a) I. Goldberg, Ber. Dtsch. Chem. Ges. 1906, 39, 1691–
692; b) H. S. Freeman, J. R. Butler, L. D. Freedman, J.
[
1
Org. Chem. 1978, 43, 4975–4977; c) A. Ito, T. Saito, K.
Tanaka, T. Yamabe, Tetrahedron Lett. 1995, 36, 8809–
[
6] For a review, see: a) A. Guꢄrinot, S. Reymond, J. Cossy,
Eur. J. Org. Chem. 2012, 19–28. For some selected exam-
ples, see: b) J. J. Ritter, P. P. Minieri, J. Am. Chem. Soc.
8
812; d) M. Sugahara, T. Ukita, Chem. Pharm. Bull.
1
997, 45, 719–721; e) J. H. M. Lange, L. J. F. Hofmeyer,
1
948, 70, 4045–4048; c) J. J. Ritter, J. Kalish, J. Am.
F. A. S. Hout, S. J. M. Osnabrug, P. C. Verveer, C. G.
Chem. Soc. 1948, 70, 4048–4050; d) A. I. Meyers, J. J.
Ritter, J. Org. Chem. 1958, 23, 1918–1922; e) A. I.
Meyers, J. Org. Chem. 1960, 25, 1147–1151; f) S. J.
Chang, Org. Process Res. Dev. 1999, 3, 232–234; g) K. L.
Reddy, Tetrahedron Lett. 2003, 44, 1453–1455; h) M. Shi,
G.-Q. Tian, Tetrahedron Lett. 2006, 47, 8059–8062; i) R.
Sanz, A. Martꢂnez, V. Guilarte, J. M. ꢃlvarez-Guitiꢄrrez,
F. Rodrꢂguez, Eur. J. Org. Chem. 2007, 4642–4645; j) P.
Rubenbauer, T. Bach, Chem. Commun. 2009, 2130–
Kruse, R. W. Feenstra, Tetrahedron Lett. 2002, 43, 1101–
1
104.
[
[
3] For the reviews, see: a) Y. Jiang, D. Ma, in: Catalysis
without Precious Metals, (Ed.: R. M. Bullock), Wiley-
Blackwell, Weinheim, 2010, pp 213–233; b) Y. Wang, J.
Zeng, X. Cui, Chin. J. Org. Chem. 2010, 30, 181–199 (in
Chinese).
4] a) A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J.
Am. Chem. Soc. 2001, 123, 7727–7729; b) A. Klapars, X.
Huang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124,
2
132; k) M. Barbero, S. Bazzi, S. Cadamuro, S. Dughera,
Eur. J. Org. Chem. 2009, 430–436; l) Q. Michaudel, D.
Thevenet, P. S. Baran, J. Am. Chem. Soc. 2012, 134,
7
421–7428; c) K. R. Crawford, A. Padwa, Tetrahedron
Lett. 2002, 43, 7365–7368; d) B. Mallesham, B. M.
Rajesh, P. R. Reddy, D. Srinivas, S. Trehan, Org. Lett.
2
547–2550.
7] a) G. Evindar, R. A. Batey, J. Org. Chem. 2006, 71,
802; b) P. Saha, T. Ramana, N. Purkait, M. A. Ali, R.
[
2
003, 5, 963–965; e) W. Deng, Y.-F. Wang, Y. Zou, L.
1
Liu, Q.-X. Guo, Tetrahedron Lett. 2004, 45, 2311–2315;
f) R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, H.
Mehdinejad, Synlett 2004, 1517–1520; g) E. R. Strieter,
D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc.
Paul, T. Punniyamurthy, J. Org. Chem. 2009, 74, 8719;
c) M. L. Kantam, G. T. Venkanna, K. B. Shiva Kumar, V.
Balasubrahmanyam, S. Bhargava, Synlett 2009, 1753;
d) G. Altenhoff, F. Glorius, Adv. Synth. Catal. 2004, 346,
2
005, 127, 4120–4121; h) N. Zheng, S. L. Buchwald, Org.
1
661–1664.
Lett. 2007, 9, 4749–4751; i) R. A. Altman, A. M. Hyde,
X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130,
[
[
8] The nitriles can be hydrolyzed only under basic condi-
tons without the aid of copper catalyst [for the control
experiments, see Eqs. (3) and (4) in the Supporting In-
formation].
9
613–9620; j) C.-Z. Tao, J. Li, Y. Fu, L. Liu, Q.-X. Guo,
Tetrahedron Lett. 2008, 49, 70–75; k) E. R. Strieter, B.
Bhayana, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131,
9] a) G. Lefꢅvre, G. Franc, A. Tlili, C. Adamo, M. Taillefer,
7
8–88; l) C. Wang, L. Liu, W. Wang, D.-S. Ma, H. Zhang,
I. Ciofini, A. Jutand, Organometallics 2012, 31, 7694–
Molecules 2010, 15, 1154–1160; m) M. Wang, H. Yu, X.
You, J. Wu, Z. Shang, Chin. J. Chem. 2012, 30, 2356–
7
707; b) J. Garcꢂa-Lꢆpez, V. YaÇez-Rodrꢂguez, L. Roces,
2
362.
S. Garcꢂa-Granda, A. Martꢂnez, A. Guevara-Garcꢂa,
G. R. Castro, F. Jimꢄnez-Villacorta, M. J. Iglesias, F. L.
Ortiz, J. Am. Chem. Soc. 2010, 132, 10665–10667;
c) A. E. King, L. M. Huffman, A. Casitas, M. Costas, X.
Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068–
12073.
[
5] For a review, see: a) T. J. Ahmed, S. M. M. Knapp, D. R.
Tyler, Coord. Chem. Rev. 2011, 255, 949–974. For some
selected examples, see: b) F. Chemat, M. Poux, J.
Berlan, J. Chem. Soc. Perkin Trans. 2 1996, 1781–1784;
c) L. Siegfried, A. Comparone, M. Neuburger, T. A.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢁ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5
ÞÞ
These are not the final page numbers!