286
Y. Nishihara et al. / Journal of Organometallic Chemistry 620 (2001) 282–286
J.L. Mascarenas, L.A. Sarandeses, L. Castedo, A. Mourino,
Tetrahedron 47 (1991) 3485. (i) M.L. Curtin, W.H. Okamura, J.
Am. Chem. Soc. 113 (1991) 6958. (j) J.T. Lin, J.J. Wu, C.-S. Li,
Y.S. Wen, K.-J. Lin, Organometallics 15 (1996) 5028.
[4] M. Cirrano, J.A.K. Howard, J.L. Spencer, F.G.A. Stone, H.
Vadepohl, J. Chem. Soc. Dalton Trans. (1979) 1749.
mild conditions. The resulting species containing a Cu–
C(sp) bond are probably involved in the cross-coupling
reactions of alkynylsilane with acyl chlorides and aryl
triflates reported recently and in the oxidative homo-
coupling of RCꢀCSiMe3 giving conjugated diynes.
[5] (a) T. Rappert, O. Nu¨rnberg, H. Werner, Organometallics 12
(1993) 1359. (b) M. Baum, B. Windmu¨ller, H. Werner, Z.
Naturforsch. 49B (1994) 859.
[6] D. Huang, R.H. Heyn, J.C. Bollinger, K.G. Caulton,
Organometallics 16 (1997) 292.
Acknowledgements
[7] H. Ito, A. Hosomi, Private communication.
This work was partially supported by a Grant-in-Aid
for Scientific Research (A) no. 07405042 from the Min-
istry of Education, Science, Sports, and Culture, Japan.
[8] [Cu(CꢀCPh)]n has been prepared from the reaction of a pheny-
lacetylene with NH3 aqueous solution of a copper(I) iodide; see,
D.C. Qwsley, C.E. Castro, Org. Synth. 52 (1972) 128. The IR
spectrum of [Cu(CꢀCPh)]n; see, V.T. Aleksanyan, I.A. Garbu-
zova, I.R. Gol’ding, A.M. Sladkov, Spectrochim. Acta Part A 31
(1975) 517.
References
[9] Q. Liu, D.J. Burton, Tetrahedron Lett. 38 (1997) 4371.
[10] R.D. Stephens, C.E. Castro, J. Org. Chem. 28 (1963) 3313.
[11] Structure of alkynylcopper complexes: (a) G.E. Coates, M.L.H.
Green, K. Wade, Organometallic Compounds, vol. 2, Methuen,
London, 1968, p. 274. Other examples for alkynylcopper com-
plexes; see (b) P.W.R. Cornfield, H.M.M. Shearer, Acta Crystal-
logr. 21 (1966) 957. (c) L. Naldini, F. Demartin, M. Manassero,
M. Sansoni, G. Rassu, M.A. Zoroddu, J. Organomet. Chem. 279
(1985) C42. (d) M.P. Gamasa, J. Gimeno, E. Lastra, X. Solans,
J. Organomet. Chem. 346 (1988) 277. (e) J. Diez, M.P. Gamasa,
J. Gimeno, E. Lastra, A. Aguirre, S. Garc´ıa-Granda,
Organometallics 12 (1993) 2213.
[1] (a) H. Ito, K. Arimoto, H. Sensui, A. Hosomi, Tetrahedron Lett.
38 (1997) 3977. (b) H. Ito, A. Hosomi, J. Synth. Org. Chem. Jpn.
58 (2000) 274.
[2] Y. Nishihara, K. Ikegashira, K. Hirabayashi, J. Ando, A. Mori,
T. Hiyama, J. Org. Chem. 65 (2000) 1780.
[3] (a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett.
(1975) 4467. (b) S. Takahashi, Y. Kuroyama, K. Sonogashira,
N. Hagihara, Synthesis (1980) 627. (c) K. Sonogashira, S. Taka-
hashi, J. Syn. Org. Chem. Jpn. 51 (1993) 1053 (in Japanese). The
Sonogashira reaction; see, (d) I.B. Campbell, in: R.J.K. Taylor
(Eds.), Organocopper Reagents A Practical Approach, Oxford
University Press, Oxford, 1994, pp. 217–235. (e) E.T. Sabourin,
A. Onopchenko, J. Org. Chem. 48 (1983) 5135. (f) S.J. Havens,
P.M. Hergenrother, J. Org. Chem. 50 (1985) 1763. (g) S.L.
Schreiber, L.L. Kiessling, J. Am. Chem. Soc. 110 (1988) 631. (h)
[12] K. Ikegashira, Y. Nishihara, K. Hirabayashi, A. Mori, T.
Hiyama, Chem. Commun. (1997) 1039.
[13] (a) S. Kobayashi, K. Nishio, Tetrahedron Lett. 34 (1993) 3453.
(b) S. Kobayashi, K. Nishio, J. Org. Chem. 59 (1994) 6620.
.