Direct alkynyl group transfer from silicon to copper: New preparation method of alkynylcopper (I) reagents

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3977-3980

  Ito, Hajime ^a   Arimoto, Kikuo ^a   Sensui, Hiro Omi ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL PHENYL KETONE; ALKYNYL GROUP; ALKYNYLCOPPER; COPPER; REAGENT; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0030990486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00794-6     Document Type: Article

References (13)

1. Studies on Organosilicon Chemistry. No. 134. For No. 133, see: Hojo, M.; Aihara, H. J. Am. Chem. Soc. 1996, 118, 3533.
2. Studies on Organosilicon Chemistry. No. 134. For No. 133, see: Hojo, M.; Aihara, H. J. Am. Chem. Soc. 1996, 118, 3533.
3. Taylor, R. J. K. Organocopper Reagents Organocopper Reagents: A Practical Approach. Oxford University Press: Oxford 1994.
4. Trifluoromethylation of organic halides with a trifluoromethylsilane using KF and CuI was reported as a special case. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91.
5. A possibility of the generation of an alkynylcopper(I) intermediate in the phenylation of an alkynylsilane with triphenylbismuth difluoride was reported without obvious evidence of the group transfer. Lermontov, S. A.; Rakov, I. M.; Zefirov, N. S.; Stang, P. J. Tetrahedron Lett. 1996, 37, 4051.
6. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer Verlag: Berlin, 1983; pp. 129-158.
7. Macomber, D. W.; Rausch, M. D. J. Am. Chem. Soc. 1983, 105, 5325.
8. The spectroscopic data are identical with those of the authentic sample prepared by the literature method. Sazonova, V. A.; Kronrod, N. Ya. Zh. Obshch. Khim. 1956, 26, 1876.
9. For the formation of alkynylsilanes from alkynylcopper(I) and chlorosilanes, see: Sugita, H.; Hatanaka, Y.; Hiyama, T. Chem. Lett. 1996, 379.
10. (a) Birkofer, L.; Ritter, A.; Uhlenbrauck, H. Chem. Ber. 1963, 96, 3280.
11. (b) Utimoto, K.; Tanaka, M.; Kitai, M.; Nozaki, H. Tetrahedron Lett. 1978, 2301.
12. For the acylations using copper (I) acetylides prepared from terminal alkynes, see: Posner, G. H. Org. React. 1975, 22, 380.
13. 3 (400 mg, 3.0 mmol) at room temperature under nitrogen. After stirring for 4 h, 1f completely disappeared. After the separation of products by preparative TLC followed by usual workup, only desilylation products were obtained. (eq. 5) formula represented