Organic & Biomolecular Chemistry
Paper
M. Bhattacharjee, Tetrahedron Lett., 2009, 50, 4863;
(e) M. Jimenez-Tenorio, M. C. Puerta and P. Valerga, Orga-
nometallics, 2009, 28, 2787; (f) L. D. Field, A. M. Magill,
T. K. Shearer, S. J. Dalgarno and M. M. Bhadbhade,
Eur. J. Inorg. Chem., 2011, 3503; (g) A. Coniglio, M. Bassetti,
S. E. García-Garrido and J. Gimeno, Adv. Synth. Catal.,
2012, 354, 148.
Notes and references
1 (a) Modern Acetylene Chemistry, ed. P. J. Stang and F. Die-
derich, VCH, New York, 1995; (b) Chemistry and Biology of
Naturally Occurring Acetylenes and Related Compounds, ed. J.
Lam, H. Breteler, T. Arnason and L. Hansen, Elsevier,
Amsterdam, 1998.
2 (a) V. Ritleng, C. Sirlin and M. Pfeffer, Chem. Rev., 2002, 14 (a) P. Krüger and H. Werner, Eur. J. Inorg. Chem., 2004, 481;
102, 1731; (b) H. Katayama and F. Ozawa, Coord. Chem.
Rev., 2004, 248, 1703; (c) P. Wessig and G. Müller, Chem.
Rev., 2008, 108, 2051.
3 (a) P. Siemsen, R. C. Livingston and F. Diederich, Angew.
Chem., Int. Ed., 2000, 39, 2632; (b) H. Katayama,
M. Nakayama, T. Nakano, C. Wada, K. Akamatsu and
(b) C.-C. Lee, Y.-C. Lin, Y.-H. Liu and Y. Wang, Organometal-
lics, 2005, 24, 136; (c) M. Schäfer, J. Wolf and H. Werner,
Dalton Trans., 2005, 1468; (d) W. Weng, C. Guo,
R. Çelenligil-Çetin, B. M. Foxman and O. V. Ozerov, Chem.
Commun., 2006, 197; (e) H. M. Peng, J. Zhao and X. Li, Adv.
Synth. Catal., 2009, 351, 1371.
F. Ozawa, Macromolecules, 2004, 37, 13; (c) N. K. Pahadi, 15 (a) R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-
D. H. Camacho, I. Nakamura and Y. Yamamoto, J. Org.
Chem., 2006, 71, 1152; (d) Y. Liu, M. Nishiura, Y. Wang and
Z. Hou, J. Am. Chem. Soc., 2006, 128, 5592.
Jespersen and A. S. Goldman, J. Am. Chem. Soc., 2007, 129,
853; (b) K. Ogata and A. J. Toyota, Organomet. Chem., 2007,
692, 4139; (c) C.-H. Jun, Z. Lu and R. H. Crabtree, Tetra-
hedron Lett., 1992, 33, 7119.
4 S. Saito and Y. Yamamoto, Chem. Rev., 2000, 100, 2901.
5 (a) G. Zweifel and N. L. Polston, J. Am. Chem. Soc., 1970, 92, 16 S. Ogoshi, M. Ueta, M.-A. Oka and H. Kurosawa, Chem.
4068; (b) J. A. Cabezas and A. C. Oehlschlager, Synthesis,
1999, 107.
6 K. C. Nicolau, W. M. Dai, S. C. Tsay, V. A. Estevez and
W. Wrasidlo, Science, 1992, 256, 1172.
Commun., 2004, 2732.
17 (a) B. M. Trost, C. Chan and G. Ruhter, J. Am. Chem. Soc.,
1987, 109, 3486; (b) B. M. Trost, M. T. Sorum, C. Chan,
A. E. Harms and G. Ruhter, J. Am. Chem. Soc., 1997, 119,
698; (c) V. Gevorgyan, U. Radhakrishnan, A. Takeda,
M. Rubina, M. Rubin and Y. Yamamoto, J. Org. Chem.,
2001, 66, 2835; (d) M. Rubina and V. Gevorgyan, J. Am.
Chem. Soc., 2001, 123, 11107; (e) C. Yang and S. P. Nolan,
J. Org. Chem., 2002, 67, 591; (f) H. Katayama,
M. Nakayama, T. Nakano, C. Wada, K. Akamatsu and
F. Ozawa, Macromolecules, 2004, 37, 13; (g) Y.-T. Wu,
W.-C. Lin, C.-J. Liu and C.-Y. Wua, Adv. Synth. Catal., 2008,
350, 1841; (h) T.-H. Hsiao, T.-L. Wu, S. Chatterjee,
C.-Y. Chiu, H. M. Lee, L. Bettucci, C. Bianchini and
W. Oberhauser, J. Organomet. Chem., 2009, 694, 40;
(i) C. Jahier, O. V. Zatolochnaya, N. V. Zvyagintsev,
V. P. Ananikov and V. Gevorgyan, Org. Lett., 2012, 14, 2486.
7 (a) A. Alexakis, G. Cahiez and J. F. Normant, Synthesis,
1979, 826; (b) P. J. Stang and T. Kitamura, J. Am. Chem. Soc.,
1987, 109, 7561; (c) S.-K. Kang, W.-Y. Kim and X. Jiao, Syn-
thesis, 1998, 1252; (d) C. C. Silveira, A. L. Braga, A. S. Vieira
and G. Zeni, J. Org. Chem., 2003, 68, 662; (e) M. Hoshi,
H. Nakayabu and K. Shirakawa, Synthesis, 2005, 1991.
8 (a) U. Halbes, P. Bertus and P. Pale, Tetrahedron Lett., 2001,
42, 8641; (b) J. A. Marshall, H. R. Chobanian and
M. M. Yanik, Org. Lett., 2001, 3, 4107; (c) N. Kakusawa,
K. Yamaguchi and J. Kurita, J. Organomet. Chem., 2005,
690, 2956–2966.
9 (a) M. Alami, F. Ferri and G. Linstrumelle, Tetrahedron
Lett., 1993, 34, 6403; (b) J. P. Genet and M. Savignac,
J. Organomet. Chem., 1999, 576, 305; (c) U. Halbes, P. Bertus 18 (a) H. J. Heeres and J. H. Teuben, Organometallics, 1991,
and P. Pale, Tetrahedron Lett., 2001, 42, 8641; (d) A. Mori,
T. Shimada, T. Kondo and A. Sekiguchi, Synlett, 2001, 649;
(e) T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato and
I. Ryu, Org. Lett., 2002, 4, 1691; (f) M. Feuerstein,
L. Chahen, H. Doucet and M. Santelli, Tetrahedron, 2006,
62, 112; (g) Y. Liu, J. Yang and W. Bao, Eur. J. Org. Chem.,
2009, 5317.
10, 1980; (b) M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki
and T. Miyamoto, J. Am. Chem. Soc., 2003, 125, 1184;
(c) C. G. J. Tazelaar, S. Bambirra, D. Leusen, A. Meetsma,
B. Hessen and J. H. Teuben, Organometallics, 2004, 23, 936;
(d) S. Ge, V. F. Quiroga Norambuena and B. Hessen, Orga-
nometallics, 2007, 26, 6508.
19 (a) A. Haskel, T. Straub, A. K. Dash and M. S. Eisen, J. Am.
Chem. Soc., 1999, 121, 3014; (b) J. Wang, M. Kapon,
J. C. Berthet, M. Ephritikhine and M. S. Eisen, Inorg. Chim.
Acta, 2002, 334, 183.
20 (a) A. V. Korolev, I. A. Guzei and R. F. Jordan, J. Am. Chem.
Soc., 1999, 121, 11605; (b) A. K. Dash and M. S. Eisen, Org.
Lett., 2000, 2, 737.
10 R. H. Platel and L. L. Schafer, Chem. Commun., 2012, 48,
10609.
11 M. Yoshida and R. F. Jordan, Organometallics, 1997, 16,
4508.
12 A. Kawata, Y. Kuninobu and K. Takai, Chem. Lett., 2009, 38,
836.
13 (a) Y. Gao and R. J. Puddephatt, Inorg. Chim. Acta, 2003, 21 (a) B. M. Trost, Science, 1991, 254, 1471; (b) B. M. Trost,
350, 101; (b) M. Bassetti, C. Pasquini, A. Raneri and Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
D. Rosato, J. Org. Chem., 2007, 72, 4558; (c) A. Hijazi, 22 For recent reviews on iron catalysis, see: (a) C. Bolm,
K. Parkhomenko, J.-P. Djukic, A. Chemmi and M. Pfeffer,
Adv. Synth. Catal., 2008, 350, 1493; (d) J. Tripathy and
J. Legros, J. Le Paih and L. Zani, Chem. Rev., 2004, 104,
6217; (b) A. Fürstner and R. Martin, Chem. Lett., 2005, 34,
This journal is © The Royal Society of Chemistry 2014
Org. Biomol. Chem., 2014, 12, 1812–1822 | 1821