FULL PAPERS
1996, 61, 962–968; d) S. E. Denmark, M. T. Burk, A. J.
Hoover, J. Am. Chem. Soc. 2010, 132, 1232–1233.
136, 5627–5630; b) D. Huang, H. Wang, F. Xue, H.
Guan, L. Li, X. Peng, Y. Shi, Org. Lett. 2011, 13, 6350–
6353; c) S. E. Denmark, M. T. Burk, Org. Lett. 2012, 14,
256–259.
[5] For recent reviews of halocyclization, see: a) S. E. Den-
mark, M. T. Burk, Proc. Natl. Acad. Sci. USA 2010,
107, 20655–20660; b) S. E. Denmark, W. E. Kuester,
M. T. Burk, Angew. Chem. 2012, 124, 11098–11113;
Angew. Chem. Int. Ed. 2012, 51, 10938–10953; c) G. F.
Chen, S. M. Ma, Angew. Chem. 2010, 122, 8484–8486;
Angew. Chem. Int. Ed. 2010, 49, 8306–8308; d) A. Cas-
tellanos, S. P. Fletcher, Chem. Eur. J. 2011, 17, 5766–
5776; e) C. K. Tan, L. Zhou, Y.-Y. Yeung, Synlett 2011,
1335–1339; f) U. Hennecke, Chem. Asian J. 2012, 7,
456–465; g) C. K. Tan, Y.-Y. Yeung, Chem. Commun.
2013, 49, 7985–7996; h) S. A. Snyder, D. S. Treitler,
A. P. Brucks, Aldrichimica Acta 2011, 44, 27–40; i) K.
Murai, H. Fujioka, Heterocycles 2013, 87, 763–805.
[6] For advances in halocyclization, see: a) A. Sakakura,
A. Ukai, K. Ishihara, Nature 2007, 445, 900–903; b) J.
Haas, S. Bissmire, T. Wirth, Chem. Eur. J. 2005, 11,
5777–5785; c) J. Haas, S. Piguel, T. Wirth, Org. Lett.
2002, 4, 297–300; d) D. C. Whitehead, R. Yousefi, A.
Jaganathan, B. Borhan, J. Am. Chem. Soc. 2010, 132,
3298–3300; e) G. E. Veitch, E. N. Jacobsen, Angew.
Chem. 2010, 122, 7490–7493; Angew. Chem. Int. Ed.
2010, 49, 7332–7335; f) L. Zhou, C. K. Tan, X. Jiang, F.
Chen, Y.-Y. Yeung, J. Am. Chem. Soc. 2010, 132,
15474–15476; g) K. Murai, T. Matsushita, A. Naka-
mura, S. Fukushima, M. Shimura, H. Fujioka, Angew.
Chem. 2010, 122, 9360–9363; Angew. Chem. Int. Ed.
2010, 49, 9174–9177; h) W. Zhang, S. Zheng, N. Liu,
J. B. Werness, I. A. Guzei, W. Tang, J. Am. Chem. Soc.
2010, 132, 3664–3665; i) S. H. Kang, S. B. Lee, C. M.
Park, J. Am. Chem. Soc. 2003, 125, 15748–15749; j) M.
Wang, L. X. Gao, W. P. Mai, A. X. Xia, F. Wang, S. B.
Zhang, J. Org. Chem. 2004, 69, 2874–2876; k) H. Y.
Kwon, C. M. Park, S. B. Lee, J. H. Youn, S. H. Kang,
Chem. Eur. J. 2008, 14, 1023–1028; l) Z. Ning, R. Jin, J.
Ding, L. Gao, Synlett 2009, 2291–2994; m) X. Jiang,
C. K. Tan, L. Zhou, Y.-Y. Yeung, Angew. Chem. 2012,
124, 7891–7895; Angew. Chem. Int. Ed. 2012, 51, 7771–
7775; n) Y. Zhao, X. Jiang, Y.-Y. Yeung, Angew. Chem.
2013, 125, 8759–8764; Angew. Chem. Int. Ed. 2013, 52,
8597–8601.
[8] For 4-membered-ring halocyclization, see: a) S. Melle-
gaard, J. A. Tunge, J. Org. Chem. 2004, 69, 1047; b) M.
Zhu, L. Li, J. Tong, H. Zhang, Chin. Chem. Lett. 2011,
22, 431–434.
[9] For examples of dihalogenation, see: K. C. Nicolaou,
N. L. Simmons, Y. Ying, P. M. Heretsch, J. S. Chen, J.
Am. Chem. Soc. 2011, 133, 8134–8137.
[10] For selected examples of halogenation/semipinacol re-
arrangement, see: a) Z.-M. Chen, Q.-W. Zhang, Z.-H.
Chen, H. Li, Y.-Q. Tu, F.-W. Zhang, J.-M. Tian, J. Am.
Chem. Soc. 2011, 133, 8818–8821; b) B. L. Maroto, S. de
La Moya Cerero, A. G. Martꢄnez, A. G. Fraile, E. T.
Vilar, Tetrahedron: Asymmetry 2000, 11, 3059–3063;
c) L. A. Paquette, D. R. Owen, R. T. Bibart, C. K. See-
kamp, A. L. Kahane, J. C. Lanter, M. A. Corral, J. Org.
Chem. 2001, 66, 2828–2834; d) C.-A. Fan, Y.-Q. Tu, Z.-
L. Song, E. Zhang, L. Shi, M. Wang, B.-M. Wang, S.-Y.
Zhang, Org. Lett. 2004, 6, 4691–4694; e) X.-D. Hu, Y.-
Q. Tu, E. Zhang, S.-H. Gao, S.-H. Wang, A.-X. Wang,
C.-A. Fan, M. Wang, Org. Lett. 2006, 8, 1823–1825;
f) T. Snape, Chem. Soc. Rev. 2007, 36, 1823–1842;
g) P. B. Hurley, G. R. Dake, J. Org. Chem. 2008, 73,
4131–4138; h) P. B. Hurley, G. R. Dake, Synlett 2003,
2131–2134.
[11] For NCS mediated oxidation, see: a) J. Einhorn, C.
Einhorn, R. Ratajczak, J.-L. Pierre, J. Org. Chem. 1996,
61, 7452–7454; b) K. S. Kim, I. H. Cho, B. K. Yoo, Y. H.
Song, C. S. Hahn, J. Chem. Soc. Chem. Commun. 1984,
762–763; c) K. Takaki, M. Yasumura, K. Negoro, J.
Org. Chem. 1983, 48, 54–57.
[12] For NBS mediated oxidation, see: a) D. Xu, S. Wang,
Z. Shen, C. Xia, W. Sun, Org. Biomol. Chem. 2012, 10,
2730–2732; b) N. S. Krishnaveni, K. Surendra, K. R.
Rao, Adv. Synth. Catal. 2004, 346, 346–350; c) R. Filler,
Chem. Rev. 1963, 63, 21–43; d) E. A. Couladouros,
M. P. Georgiadis, J. Org. Chem. 1986, 51, 2725–2727;
e) B. W. Finucane, J. B. Thomson, J. Chem. Soc. Perkin
Trans. 1 1972, 1856–1862; f) L. F. Fieser, W. P. Schneid-
er, W.-Y. Huang, J. Am. Chem. Soc. 1953, 75, 124–127;
g) E. J. Corey, M. Ishiguro, Tetrahedron Lett. 1979, 20,
2745–2748.
[7] For examples of haloetherification, see: a) Z. Ke, C. K.
Tan, F. Chen, Y.-Y. Yeung, J. Am. Chem. Soc. 2014,
Adv. Synth. Catal. 0000, 000, 0 – 0
6
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
These are not the final page numbers!