-
1
-
-
0026418434
-
-
B. M. Trost, Science 1991, 254, 1471;
-
(1991)
Science
, vol.254
, pp. 1471
-
-
Trost, B.M.1
-
3
-
-
0026718016
-
-
K. C. Nicolaou, W. M. Dai, S. C. Tsay, V. A. Estevez, W. Wrasidlo, Science 1992, 256, 1172.
-
(1992)
Science
, vol.256
, pp. 1172
-
-
Nicolaou, K.C.1
Dai, W.M.2
Tsay, S.C.3
Estevez, V.A.4
Wrasidlo, W.5
-
4
-
-
33645452006
-
-
For recent examples of dimerization of terminal alkynes, see: Rh a W. Weng, C. Guo, R. Çelenligil-Çetin, B. M. Foxman, O. V. Ozerov, Chem. Commun. 2006, 197;
-
For recent examples of dimerization of terminal alkynes, see: Rh a) W. Weng, C. Guo, R. Çelenligil-Çetin, B. M. Foxman, O. V. Ozerov, Chem. Commun. 2006, 197;
-
-
-
-
5
-
-
12344324618
-
-
b) C.-C. Lee, Y.-C. Lin, Y.-H. Liu, Y. Wang, Organometallics 2005, 24, 136;
-
(2005)
Organometallics
, vol.24
, pp. 136
-
-
Lee, C.-C.1
Lin, Y.-C.2
Liu, Y.-H.3
Wang, Y.4
-
6
-
-
33846611597
-
-
Ir c R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853;
-
Ir c) R. Ghosh, X. Zhang, P. Achord, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, J. Am. Chem. Soc. 2007, 129, 853;
-
-
-
-
7
-
-
20444471183
-
-
d) M. V. Jiménez, E. Sola, F. J. Lahoz, L. A. Oro, Organometallics 2005, 24, 2722;
-
(2005)
Organometallics
, vol.24
, pp. 2722
-
-
Jiménez, M.V.1
Sola, E.2
Lahoz, F.J.3
Oro, L.A.4
-
8
-
-
0000501827
-
-
e) T. Ohmura, S. Yorozuya, Y. Yamamoto, N. Miyaura, Organometallics 2000, 19, 365;
-
(2000)
Organometallics
, vol.19
, pp. 365
-
-
Ohmura, T.1
Yorozuya, S.2
Yamamoto, Y.3
Miyaura, N.4
-
9
-
-
24944453067
-
-
Ru f X. Chen, P. Xue, H. H. Y. Sung, I. D. Williams, M. Peruzzini, C. Bianchini, G. Jia, Organometallics 2005, 24, 4330;
-
Ru f) X. Chen, P. Xue, H. H. Y. Sung, I. D. Williams, M. Peruzzini, C. Bianchini, G. Jia, Organometallics 2005, 24, 4330;
-
-
-
-
11
-
-
0038157006
-
-
h) M. Bassetti, S. Marini, J. Díaz, M. P. Gamasa, J. Gimeno, Y. Rodríguez-Álvarez, S. García-Granda, Organometallics 2002, 21, 4815;
-
(2002)
Organometallics
, vol.21
, pp. 4815
-
-
Bassetti, M.1
Marini, S.2
Díaz, J.3
Gamasa, M.P.4
Gimeno, J.5
Rodríguez-Álvarez, Y.6
García-Granda, S.7
-
12
-
-
11144300921
-
-
Ni i S. Ogoshi, M. Ueta, M. Oka, H. Kurosawa, Chem. Commun. 2004, 2732;
-
Ni i) S. Ogoshi, M. Ueta, M. Oka, H. Kurosawa, Chem. Commun. 2004, 2732;
-
-
-
-
13
-
-
0037169069
-
-
Pd j C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591;
-
Pd j) C. Yang, S. P. Nolan, J. Org. Chem. 2002, 67, 591;
-
-
-
-
15
-
-
24144490998
-
-
other metals; l K. Komeyama, T. Kawabata, K. Takehira, K. Takaki, J. Org. Chem. 2005, 70, 7260;
-
other metals; l) K. Komeyama, T. Kawabata, K. Takehira, K. Takaki, J. Org. Chem. 2005, 70, 7260;
-
-
-
-
16
-
-
0037419829
-
-
m) M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184;
-
(2003)
J. Am. Chem. Soc
, vol.125
, pp. 1184
-
-
Nishiura, M.1
Hou, Z.2
Wakatsuki, Y.3
Yamaki, T.4
Miyamoto, T.5
-
18
-
-
25144435810
-
-
Cross-dimerization of terminal alkynes, see: a
-
Cross-dimerization of terminal alkynes, see: a) H. Katayama, H. Yari, M. Tanaka, F. Ozawa, Chem. Commun. 2005, 4336;
-
(2005)
Chem. Commun
, pp. 4336
-
-
Katayama, H.1
Yari, H.2
Tanaka, M.3
Ozawa, F.4
-
19
-
-
1842473945
-
-
b) J. Wang, M. Kapon, J. C. Berthet, M. Ephritikhine, M. S. Eisen, Inorg. Chim. Acta 2002, 334, 183;
-
(2002)
Inorg. Chim. Acta
, vol.334
, pp. 183
-
-
Wang, J.1
Kapon, M.2
Berthet, J.C.3
Ephritikhine, M.4
Eisen, M.S.5
-
20
-
-
0001571404
-
-
c) M. Akita, H. Yasuda, A. Nakamura, Bull. Chem. Soc. Jpn. 1984, 57, 480.
-
(1984)
Bull. Chem. Soc. Jpn
, vol.57
, pp. 480
-
-
Akita, M.1
Yasuda, H.2
Nakamura, A.3
-
21
-
-
0031046817
-
-
For examples of the addition of terminal alkynes to electron-deficient alkynes, see: a B. M. Trost, M. T. Sorum, C. Chan, A. E. Harms, G. Rühter, J. Am. Chem. Soc. 1997, 119, 698, and references cited therein;
-
For examples of the addition of terminal alkynes to electron-deficient alkynes, see: a) B. M. Trost, M. T. Sorum, C. Chan, A. E. Harms, G. Rühter, J. Am. Chem. Soc. 1997, 119, 698, and references cited therein;
-
-
-
-
23
-
-
20044373868
-
-
c) T. Hirabayashi, S. Sakaguchi, Y. Ishii, Adv. Synth. Catal. 2005, 347, 872;
-
(2005)
Adv. Synth. Catal
, vol.347
, pp. 872
-
-
Hirabayashi, T.1
Sakaguchi, S.2
Ishii, Y.3
-
25
-
-
0001344076
-
-
For an example of the addition of terminal alkynes to internal alkynes, see
-
For an example of the addition of terminal alkynes to internal alkynes, see: C. S. Yi, N. Liu, Organometallics 1998, 17, 3158.
-
(1998)
Organometallics
, vol.17
, pp. 3158
-
-
Yi, C.S.1
Liu, N.2
-
26
-
-
34547184427
-
-
Very recently, Miura reported rhodium-catalyzed cross dimerization of silylacetylenes and internal alkynes: T. Katagiri, H. Tsurugi, A. Funayama, T. Satoh, and M. Miura, Chem. Lett. 2007, 36, 830. Although the present reaction in this manuscript is similar to that reported by Miura, we have studied mechanistic aspects of the reaction including characterization of the intermediates in the catalytic cycle as well as its synthetic aspects.
-
Very recently, Miura reported rhodium-catalyzed cross dimerization of silylacetylenes and internal alkynes: T. Katagiri, H. Tsurugi, A. Funayama, T. Satoh, and M. Miura, Chem. Lett. 2007, 36, 830. Although the present reaction in this manuscript is similar to that reported by Miura, we have studied mechanistic aspects of the reaction including characterization of the intermediates in the catalytic cycle as well as its synthetic aspects.
-
-
-
-
27
-
-
0037042235
-
-
T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 2002, 124, 5052.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 5052
-
-
Hayashi, T.1
Takahashi, M.2
Takaya, Y.3
Ogasawara, M.4
-
28
-
-
0035840942
-
-
Similar regioselectivity was observed in the rhodium(I)-catalyzed hydroarylation of alkynes with arylboronic acids, see: T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 2001, 123, 9918.
-
Similar regioselectivity was observed in the rhodium(I)-catalyzed hydroarylation of alkynes with arylboronic acids, see: T. Hayashi, K. Inoue, N. Taniguchi, M. Ogasawara, J. Am. Chem. Soc. 2001, 123, 9918.
-
-
-
-
29
-
-
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-
-
The E geometry (> 98%) was confirmed by NOE experiments.
-
The E geometry (> 98%) was confirmed by NOE experiments.
-
-
-
-
30
-
-
5444273085
-
-
H. Werner, Coord. Chem. Rev. 2004, 248, 1693, and references cited therein;
-
a) H. Werner, Coord. Chem. Rev. 2004, 248, 1693, and references cited therein;
-
-
-
-
32
-
-
0001442058
-
-
c) J. Ohshita, K. Furumori, A. Matsuguchi, M. Ishikawa, J. Org. Chem. 1990, 55, 3277;
-
(1990)
J. Org. Chem
, vol.55
, pp. 3277
-
-
Ohshita, J.1
Furumori, K.2
Matsuguchi, A.3
Ishikawa, M.4
-
33
-
-
0001153801
-
-
d) I. P. Kavalev, K. V. Yevdakov, Y. A. Strelenko, M. G. Vinogradov, G. I. Nikishin, J. Organomet. Chem. 1990, 386, 139.
-
(1990)
J. Organomet. Chem
, vol.386
, pp. 139
-
-
Kavalev, I.P.1
Yevdakov, K.V.2
Strelenko, Y.A.3
Vinogradov, M.G.4
Nikishin, G.I.5
-
34
-
-
11344249346
-
-
For an example of an alkynylrhodium(I) complex containing 1,5-cyclooctadiene and tricyclohexylphosphine, see: M. J. Fernández, M. A. Esteruelas, M. Covarrubias, L. A. Oro, J. Organomet. Chem. 1990, 381, 275.
-
For an example of an alkynylrhodium(I) complex containing 1,5-cyclooctadiene and tricyclohexylphosphine, see: M. J. Fernández, M. A. Esteruelas, M. Covarrubias, L. A. Oro, J. Organomet. Chem. 1990, 381, 275.
-
-
-
-
35
-
-
10044256639
-
-
For examples of isolated alkynylrhodium(I) complexes, see: a) M. Schäfer, J. Wolf, H. Werner, Organometallics 2004, 23, 5713;
-
For examples of isolated alkynylrhodium(I) complexes, see: a) M. Schäfer, J. Wolf, H. Werner, Organometallics 2004, 23, 5713;
-
-
-
-
36
-
-
0000697518
-
-
b) H. Werner, J. Wolf, F. J. Garcia Alonso, M. L. Ziegler, O. Serhadli, J. Organomet. Chem. 1987, 336, 397.
-
(1987)
J. Organomet. Chem
, vol.336
, pp. 397
-
-
Werner, H.1
Wolf, J.2
Garcia Alonso, F.J.3
Ziegler, M.L.4
Serhadli, O.5
-
37
-
-
27644584950
-
-
A. Funayama, T. Satoh, M. Miura, J. Am. Chem. Soc. 2005, 127, 15354.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 15354
-
-
Funayama, A.1
Satoh, T.2
Miura, M.3
-
38
-
-
29944445197
-
-
An alkynylruthenium-complex containing, a 13C-enriched alkynyl group, see: Y.-S. Yen, Y.-C. Lin, S.-L. Huang, Y.-H. Liu, H.-L. Sung, Y. Wang, J. Am. Chem. Soc. 2005, 127, 18037
-
13C-enriched alkynyl group, see: Y.-S. Yen, Y.-C. Lin, S.-L. Huang, Y.-H. Liu, H.-L. Sung, Y. Wang, J. Am. Chem. Soc. 2005, 127, 18037.
-
-
-
-
39
-
-
33645454196
-
-
A. Kina, H. Iwamura, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 3904.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 3904
-
-
Kina, A.1
Iwamura, H.2
Hayashi, T.3
-
40
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-
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-
The addition of 1-octyne did not give the cross-dimerization product
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The addition of 1-octyne did not give the cross-dimerization product.
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41
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37349062798
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2/dpph catalyst can also be applied to the addition to unsymmetrical arylacetylenes to give the corresponding enynes in high yields, although their regioselectivity was lower. For example, the addition of 2m to 1c gave a 92% yield of the hydroalkynylation products consisting of 3cm (53%) and 4cm (47%).
-
2/dpph catalyst can also be applied to the addition to unsymmetrical arylacetylenes to give the corresponding enynes in high yields, although their regioselectivity was lower. For example, the addition of 2m to 1c gave a 92% yield of the hydroalkynylation products consisting of 3cm (53%) and 4cm (47%).
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