The Journal of Organic Chemistry
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3
4
References
5
6
7
8
(1) (a) Lian, G. Y.; Yu, B. Chem. Biodiversity. 2010, 7, 2660–2691. (b) Vrettou, M.; Gray, A. A.; Brewer, A. R. E.;
Barrett, A. G. M. Tetrahedron 2007, 63, 1487−1536. (c) Voloshchuk, T.; Farina, N. S.; Wauchope, O. R.;
Kiprowska, M.; Haberfield, P.; Greer, A. J. Nat. Prod. 2004, 67, 1141−1146.
(2) For recent examples, see: (a) Li, C.; Dian, L.; Zhang, W.; Lei, X. J. Am. Chem. Soc. 2012, 134, 12414–12417. (b)
Snyder, S. A.; Kontes, F. J. Am. Chem. Soc. 2009, 131, 1745–1752. (c) Zhang, W.; Luo, S.; Chen, Q.; Hu, H.; Jia,
X.; Zhai, H. J. Am. Chem. Soc. 2005, 127, 18–19.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(3) (a) Lee, P. H.; Seomoon, D.; Lee, K. Org. Lett. 2005, 7, 343−345. (b) Lin, G.-q.; Hong, R. J. Org. Chem. 2001, 66,
2877−2880. (c) Venkatraman, S.; Li, C.-J. Org. Lett. 1999, 1, 1133−1135. (d) Zhang, S.; Zhang, D.; Liebeskind, L.
S. J. Org. Chem. 1997, 62, 2312−2313.
(4) Kürti, L. and Czakó, B. In Strategic Applications of Named Reactions in Organic Synthesis: Background and
Detailed Mechanisms; Elsevier, Amsterdam, 2005, pp. 498–499, and references cited therein.
(5) For some dimeric methods mediated by stoichiometric amount of metal, see: (a) Li, W.-D. Z.; Ma, B. C. Org. Lett.
2005, 7, 271−274. (b) Nishino, T.; Watanabe, T.; Okada, M.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67,
966−2880. (c) Ma, J.; Chan, T.-H. Tetrahedron Lett. 1998, 39, 2499–2502. (d) Ginah, F. O.; Donovan, T. A.; Jr.,
Suchan, S. D.; Pfennig, D. R.; Ebert, G. W. J. Org. Chem. 1990, 55, 584−589. For catalytic reactions, see: (e)
Goldup, S. M.; Leigh, D. A.; McBurney, R. T.; McGonigal, P. R.; Plant, A. Chem. Sci. 2010, 1, 383–386. (f)
Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 46, 5743−5745. (g) Xu, H.; Zhao, C.; Qian, Q.;
Deng, W.; Gong, H. Chem. Sci. 2013, 4, 4022−4029. (h) Xu, X.; Cheng, D.; Pei, W. J. Org. Chem. 2006, 71,
6637−6639.
(6) Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138−2141.
(7) (a) Yan, C.-S.; Peng, Y.; Xu, X.-B.; Wang, Y.-W. Chem.−Eur. J. 2012, 18, 6039–6048, and references cited
therein (b) Xu, X.-B.; Liu, J.; Zhang, J.-J.; Wang, Y.-W.; Peng, Y. Org. Lett. 2013, 15, 550−553.
(8) For related homocoupling reactions with benzylic halides, see: (a) Chen, T.; Yang, L.; Li, L.; Huang, K.-W.
Tetrahedron 2012, 68, 6152−6157. (b) Rosales, A.; Muñoz-Bascón, J.; López-Sánchez, C.; Álvarez-Corral, M.;
Muñoz-Dorado, M.; Rodríguez-García, I.; Oltra, J. E. J. Org. Chem. 2012, 77, 4171−4176. (c) Barrero, A. F.;
Herrador, M. M.; Quílez del Moral, J. F.; Arteaga, P.; Akssira, M.; Hanbali, F. E.; Arteaga, J. F.; Diéguez, H. R.;
Sánchez, E. M. J. Org. Chem. 2007, 72, 2251−2254. For reductive homocoupling reactions with allylic halides,
see: (d) Momose, D.-i.; Iguchi, K.; Sugiyama, T.; Yamada, Y. Tetrahedron Lett. 1983, 24, 921−924. (e) Bagal, S.
K.; Adlington, R. M.; Baldwin, J. E.; Marquez, R. J. Org. Chem. 2004, 69, 9100−9108.
(9) See the CIF file in the Supporting Information for more details.
(10) (a) Barrero, A. F.; Herrador, M. M.; Quílez del Moral, J. F.; Arteaga, P.; Arteaga, J. F.; Piedra, M.; Sánchez, E. M.
Org. Lett. 2005, 7, 2301−2304. (b) Barrero, A. F.; Herrador, M. M.; Quílez del Moral, J. F.; Arteaga, P.; Arteaga, J.
F.; Diéguez, H. R.; Sánchez, E. M. J. Org. Chem. 2007, 72, 2988−2995.
(11) (a) Zhang, J.-J.; Yan, C.-S.; Peng, Y.; Luo, Z.-B.; Xu, X.-B.; Wang, Y.-W. Org. Biomol. Chem. 2013, 11,
2498−2513. (b) Peng, Y.; Luo, Z.-B.; Zhang, J.-J.; Luo, L.; Wang, Y.-W. Org. Biomol. Chem. 2013,
DOI:10.1039/C3OB41672K.
(12) Sellars, J. D.; Steel, P. G. Eur. J. Org. Chem. 2007, 3815–3828.
(13) Kamal, A.; Laxman, E.; Ramesh Khanna, G. B.; Reddy, P. S. M. M.; Rehana, T.; Arifuddin, M.; Neelima, K.;
Kondapi A. K.; Dastidarc, S. G. Bioorg. Med. Chem. 2004, 12, 4197−4209.
(14) For recent application of this kind of ligands in Ni-catalyzed C−C coupling, see: Wang, S.; Qian, Q.; Gong, H.
Org. Lett. 2012, 14, 3352.
(15) For mechanistic studies that implicate NiI and NiIII intermediates in the related cross-coupling reactions, see: (a)
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