Organic & Biomolecular Chemistry
Paper
4 (a) L. M. Zhang and S. A. Kozmin, J. Am. Chem. Soc., 2004,
126, 11806–11807; (b) J. W. Sun, M. P. Conley, L. M. Zhang
and S. A. Kozmin, J. Am. Chem. Soc., 2006, 128, 9705–9710.
5 F. Gagosz, Org. Lett., 2005, 7, 4129–4132.
L. Jin, F. Mo, Y. Zhang and J. Wang, J. Org. Chem., 2014, 79,
1979–1988.
17 S. Bhunia, S. M. Abu Sohel, C. C. Yang, S. F. Lush, F. M. Shen
and R. S. Liu, J. Organomet. Chem., 2009, 694, 566–570.
6 (a) S. F. Kirsch, J. T. Binder, B. Crone, A. Duschek, 18 P. Garcia-Garcia, M. A. Fernandez-Rodriguez and
T. T. Haug, C. Liebert and H. Menz, Angew. Chem., Int. Ed., E. Aguilar, Angew. Chem., Int. Ed., 2009, 48, 5534–5537.
2007, 46, 2310–2313; (b) A. S. K. Hashmi and M. Wolfle, 19 FeCl3 catalyzed 1,6-enyne cyclization, see: C. Nieto-Oberhu-
Tetrahedron, 2009, 65, 9021–9029; (c) A. S. K. Hashmi,
W. B. Yang, F. Rominger and C. Invest, Angew. Chem., Int.
Ed., 2011, 50, 5761–5764; (d) A. S. K. Hashmi, W. B. Yang
ber, M. P. Munoz, S. Lopez, E. Jimenez-Nuner, C. Nevado,
E. Herrero-Gomez, M. Raducan and A. M. Echavarren,
Chem. – Eur. J., 2006, 12, 1677–1693.
and F. Rominger, Chem. – Eur. J., 2012, 18, 6576–6580; 20 (a) For N-phenylmaleimide as a ligand coordinated to plati-
(e) C. Li, Y. Zeng, H. Zhang, J. Feng, Y. Zhang and J. Wang,
Angew. Chem., Int. Ed., 2010, 49, 6413.
7 L. M. Zhang and S. A. Kozmin, J. Am. Chem. Soc., 2005, 127,
6962–6963.
num(0) complex, see M. Reinhard and M. Gerard, WO
9525734, 1995; (b) The exact function of N-phenylmalei-
mide in our reaction system remains unclear currently, see
Fig. S1 in ESI† for details.
8 S. Z. Wang and L. M. Zhang, J. Am. Chem. Soc., 2006, 128, 21 (a) For 3-OTBS-1-en-5-yne cyclization to benzene deriva-
14274–14275.
tives, see: 6a–6d; gold catalyzed 3-hydroxylated 5-en-1-yne
isomerization to benzene derivatives, see (5)
9 (a) Y. Zhang, H. Zhang, L. Y. Liu, X. Wang, W. X. Chang
and J. Li, Chem. J. Chin. Univ., 2012, 33, 2447–2451;
(b) X. Wang, L. Liu, W. Chang and J. Li, Eur. J. Org. Chem.,
2010, 5391–5396; (c) X. Wang, L. Liu, W. Chang and J. Li,
Sci. China., Ser B: Chem., 2009, 52, 1314.
(b) C. M. Grise, E. M. Rodrigue and L. Barriault, Tetra-
hedron, 2008, 64, 797–808; (c) G. J. Li and Y. H. Liu, J. Org.
Chem., 2010, 75, 2903–2909. Gold catalyzed 3-OH-1-en-yne
cyclization to benzene derivatives: (d) Y. A. Qiu,
W. Q. Kong, C. L. Fu and S. M. Ma, Org. Lett., 2012, 14,
6198–6201.
10 For a review on 1,2-alkyl migration in reactions catalyzed by
π-acids, see: (a) B. Crone and S. F. Kirsch, Chem. – Eur. J.,
2008, 14, 3514–3522; (b) D. J. Gorin and F. D. Toste, Nature, 22 Reaction of α, β-unsaturated platinum carbene intermedi-
2007, 446, 395–403; (c) P. Pyykkö, Angew. Chem., Int. Ed.,
2004, 43, 4412–4456. For selected relative ref. 4–6, and 8;
(d) Y. Wang, W. Liao, G. Huang, Y. Xia and Z. X. Yu, J. Org.
Chem., 2014, 79, 5684–5696; (e) H. Kusama, K. Ishida,
ates: (a) P. A. Allegretti and E. M. Ferreira, J. Am. Chem.
Soc., 2013, 135, 17266–17269; (b) K. Saito, H. Sogou,
T. Suga, H. Kusama and N. Iwasawa, J. Am. Chem. Soc.,
2011, 133, 689–691.
H. Funami and N. Iwasawa, Angew. Chem., Int. Ed., 2008, 23 Consecutive 1,3-cationic alkylidene migration of nonclassical
47, 4903–4905; (f) H. Kusama, E. Watanabe, K. Ishida and
N. Iwasawa, Chem. – Asian. J., 2011, 6, 2273–2277.
carbocation intermediates was proposed in the paper, see:
Q. Zhou and Y. Li, J. Am. Chem. Soc., 2014, 136, 1505–1513.
11 For selected examples, see: (a) H. Kikuchi, Y. Matsuo, 24 P. Liu, P. McCarren, P. H. Y. Cheong, T. F. Jamison and
Y. Katou, Y. Kubohara and Y. Oshima, Tetrahedron, 2012, K. N. Houk, J. Am. Chem. Soc., 2010, 132, 2050–2057.
68, 8884–8889; (b) D. A. Patrick, M. A. Ismail, R. K. Arafa, 25 A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem.
T. Wenzler, X. Zhu, T. Pandharkar, S. K. Jones, Phys., 1985, 83, 735–746.
K. A. Werbovetz, R. Brun, D. W. Boykin and R. R. Tidwell, 26 π-Acid metal catalyzed 1,3-dien-5-yne cyclization:
J. Med. Chem., 2013, 56, 5473–5494.
(a) J. W. Dankwardt, Tetrahedron Lett., 2001, 42, 5809–5812;
(b) J. J. Lian, C. C. Lin, H. K. Chang, P. C. Chen and
R. S. Liu, J. Am. Chem. Soc., 2006, 128, 9661–9667;
(c) P. Garcia-Garcia, A. Martinez, A. M. Sanjuan,
M. A. Fernandez-Rodriguez and R. Sanz, Org. Lett., 2011,
13, 4970–4973; (d) A. M. Sanjuan, P. Garcia-Garcia,
M. A. Fernandez-Rodriguez and R. Sanz, Adv. Synth. Catal.,
2013, 355, 1955–1962.
12 For selected examples, see: (a) D. L. Kays, Dalton Trans.,
2011, 40, 769–778; (b) B. M. Gridley, T. J. Blundell,
G. J. Moxey, W. Lewis, A. J. Blake and D. L. Kays, Chem.
Commun., 2013, 49, 9752–9754.
13 For selected examples, see: (a) Q. T. Fan, C. C. Wang,
Y. Han, J. F. Zhu, W. Hieringer, J. Kuttner, G. Hilt and
J. M. Gottfried, Angew. Chem., Int. Ed., 2013, 52, 4668–4672;
(b) W.-J. Hu, X.-L. Zhao, M.-L. Ma, F. Guo, X.-Q. Mi, B. Jiang 27 For both free carbenes and metal carbenes, generally, the
and K. Wen, Eur. J. Org. Chem., 2012, 1448–1454.
14 Selected papers: (a) H. Sasabe, Y. J. Pu, K. Nakayama and
J. Kido, Chem. Commun., 2009, 6655–6657; (b) H. Sasabe,
inherent migratory aptitude follows the order H > aryl >
alkyl. For reviews, see: 10a; (a) A. Nickon, Acc. Chem. Res.,
1993, 26, 84; (b) M. T. H. Liu, Acc. Chem. Res., 1994, 27, 287.
Y. Seino, M. Kimura and J. Kido, Chem. Mater., 2012, 24, 28 Selected
paper
on
m-quinquephenyl
synthesis:
1404–1406.
(a) G. F. Woods and F. T. Reed, J. Am. Chem. Soc., 1948, 71,
1348–1350; (b) M. Bennett, N. B. Sunshine and
G. F. Woods, J. Org. Chem., 1963, 28, 2514–2517. For a
report on potential functionality research, see: (c) A. S. M.
C. Rodrigues, M. A. A. Rocha and L. M. N. B. F. Santos,
J. Chem. Thermodyn., 2013, 63, 78–83.
15 C. J. F. Du, H. Hart and K. K. D. Ng, J. Org. Chem., 1986, 51,
3162–3165.
16 For selected examples, see: (a) J. M. A. Miguez, L. A. Adrio,
A. Sousa-Pedrares, J. M. Vila and K. K. Hii, J. Org. Chem.,
2007, 72, 7771–7774; (b) D. Qiu, S. Wang, S. Tang, H. Meng,
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