Copper powder-mediated homocoupling reactions of iodoacetylenes to synthesize symmetrical 1,3-butadiynes

Synthetic Communications

Volumn 38, Issue 13, 2008, Pages 2243-2251

  Xue, Song ^a   Meng, Ling Guo ^b   Guo, Qing Xiang ^b  

^a TIANJIN UNIVERSITY OF TECHNOLOGY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

1,3 Butadiynes; Copper powder; Homocoupling reaction; Iodoacetylenes

Indexed keywords

1,3 BUTADIYNE; ACETYLENE DERIVATIVE; ALKYNE; COPPER; IODOACETYLENE;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; DIMERIZATION; HOMOCOUPLING REACTION; POWDER; REACTION ANALYSIS; SYNTHESIS;

EID: 46749087863     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802026568     Document Type: Article

References (40)

1. (a) Miyawaki, K.; Goto, R.; Takagi, T.; Shibakami, M. Convergent synthesis of antiparallel cyclobolaphiles having two diacetylenes: Mimetics of membrane components that are found in archaea. Synlett 2000, 1467-1470;
2. (b) Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y.; Matsumoto, M.; Sano, Y. A new route to chiral diaryldiacetylenic liquid crystals: Preparation of iodonium salts bearing chiral alkynyl ligands and utility for chiral alkynyl transfer agents. J. Am. Chem. Soc. 1997, 119, 619-620;
3. (c) Berscheid, R.; Vögtle, F. Concave dyestuffs: A triply bridged triphenylmethyl dication. Synthesis 1992, 58-62;
4. (d) Pak, J. J.; Weakley, T. J. R.; Haley, M. M. Stepwise assembly of site specifically functionalized dehydrobenzo[18]annulenes. J. Am. Chem. Soc. 1999, 121, 8182-8192.
5. Stütz, A. Allylamine derivatives - A new class of active substances in antifungal chemotherapy. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328.
6. (a) Martin, R. E.; Diederich, F. Linear monodisperse π-conjugated oligomers: Model compounds for polymers and more. Angew. Chem., Int. Ed. Engl. 1999, 38, 1350-1377;
7. (b) Tour, J. M. Conjugated macromolecules of precise length and constitution: Organic synthesis for the construction of nanoarchitectures. Chem Rev. 1996, 96, 537-554;
8. (c) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E.; Uenishi, J. The endiandric acid cascade: Electrocyclizations in organic synthesis., 1: Stepwise, stereocontrolled total synthesis of endiandric acids A and B. J. Am. Chem. Soc. 1982, 104, 5555-5557.
9. (a) Rossi, R.; Carpita, A.; Bigelli, C. A palladium-promoted route to 3-alkyl-4-(1-alkynyl)-hexa-1,5-dyn-3-enes and/or 1,3-diynes. Tetrahedron Lett. 1985, 26, 523-526;
10. (b) Liu, Q. B.; Burton, D. J. A facile synthesis of diynes. Tetrahedron Lett. 1997, 38, 4371-4374;
11. (c) Lei, A.; Srivastava, M.; Zhang, X. Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes. J. Org. Chem. 2002, 67, 1969-1971;
12. (d) Li, J. H.; Liang, Y.; Xie, Y. X. Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions. J. Org. Chem. 2005, 70, 4393-4396;
13. (e) Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Pd-catalysed cross coupling of terminal alkynes to diynes in the absence of a stoichiometric additive. Chem. Commun. 2003, 632-633.
14. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
15. (a) Shirakawa, E.; Nakao, Y.; Murota, Y.; Hiyama, T. Palladiumiminophosphine-catalyzed homocoupling of alkynylstannanes and other organostannanes using allyl acetate or air as oxidant. J. Organomet. Chem. 2003, 670, 132-136;
16. (b) Nishihara, Y.; Okamoto, M.; Inoue, Y.; Miyazaki, M.; miyasaka, M.; Takagi, K. Synthesis of symmetrical 1,3-butadiynes by homocoupling reactions of alkynylboronates mediated by a copper salt. Tetrahedron Lett. 2005, 46, 8661-8664.
17. (a) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes. J. Org. Chem. 2000, 65, 1780-1787;
18. (b) Yoshida, H.; Yamaryo, Y.; Ohshita, J.; Kunai, A. Actiavator-free oxidative homocoupling of organosilanes catalysed by a palladium-DPPP complex. Chem. Commun. 2003, 1510-1511;
19. (c) Nishihara, Y.; Ikegashira, K.; Mori, A.; Hiyama, T. Copper(I)-catalyzed cross-coupling reaction of alkynylsilanes with 1-chloroalkynes. Tetrahedron Lett. 1998, 39, 4075-4078.
20. Damle, S. V.; Seomoon, D.; Lee, P. H. Palladium-catalyzed homocoupling reaction of 1-iodoalkynes: A simple and efficient synthesis of symmetrical 1,3-diynes. J. Org. Chem. 2003, 68, 7085-7087.
21. Yan, J. C.; Wang, L. First example of transition-metal-free Glaser-type coupling reaction. Synth. Commun. 2005, 35, 2333-2338.
22. (a) Cameron, M. D.; Bennett, G. E. Notes-use of amines in the glaser coupling reaction. J. Org. Chem. 1957, 22, 557-558;
23. (b) Eglinton, G.; Galbraith, A. R. Macrocyclic acetylenic compounds. Part I: Cyclotetradeca-1,3-diyne and related compounds. J. Chem. Soc. 1959, 889-896.
24. (a) Hay, A. S. Communications-oxidative coupling of acetylenes. J. Org. Chem. 1960, 25, 1275-1276;
25. (b) Hay, A. S. Oxidative coupling of acetylenes II. J. Org. Chem. 1962, 27, 3320-3321.
26. (a) Hébert, N.; Beck, A.; Lennox, R. B.; Just, G. A new reagent for the removal of the 4-methoxybenzyl ether: Application to the synthesis of unusual macrocyclic and bolaform phosphatidylcholines. J. Org. Chem. 1992, 57, 1777-1783;
27. (b) Menger, F. M.; Chen, X, Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. Synthesis and thermotropic properties of macrocyclic lipids related to archaebacterial membranes. J. Am. Chem. Soc. 1993, 115, 6600-6608;
28. (c) Mccallien, D. W. J.; Sanders, J. K. M. Dioxoporphyrins as supramolecular building blocks: Oligomer synthesis via preassembly on a ligand template. J. Am. Chem. Soc. 1995, 117, 6611-6612;
29. (d) Martin, R. E.; Mäder, T.; Diederich, F. Monodisperse poly(triacetylene) rods: Synthesis of a 11.9nm long molecular wire and direct determination of the effective conjugation length by UV/Vis and raman spectroscopies. Angew. Chem. Int. Ed. Ingl. 1999, 38, 817-821;
30. (e) Höger, S.; Meckenstock, A.-D.; Pellen, H. High-yield macrocyclization via glaser coupling of temporary covalent templated bisacetylenes. J. Org. Chem. 1997, 62, 4556-4557;
31. (f) Siemsen, P.; Livingston, R. C.; Diederich, F. Acetylenic coupling: A powerful tool in molecular construction. Angew. Chem. Int. Ed. 2000, 39, 2632-2657;
32. (g) Xie, X.; Phuan, P, W.; Kozlowski, M. C. Novel pathways for the formation of chiral binaphthyl polymers: Oxidative asymmetric phenolic coupling alone and in tandem with the Glaser-Hay coupling. Angew. Chem. Int. Ed. Engl. 2003, 42, 2168-2170;
33. (h) Valenti, E.; Pericas. M. A.; Serratosa, F. 1,4-Dialkoxy-1,3- butadiynes. J. Am. Chem. Soc. 1990, 112, 7405-7406.
34. Xi, M.; Bent. B. E. Mechanisms of the ullmann coupling reaction in adsorbed monolayers. J. Am. Chem. Soc. 1993, 115, 7426-7433, and references cited therein.
35. (a) Ginah, F. O.; Donovan, T. A. Jr.; Suchan, S. D.; Pfennig, D. R.; Ebert, G. W. Homocoupling of alkyl halides and cyclization of α,ω-dihaloalkanes via activated copper. J. Org. Chem. 1990, 55, 584-589;
36. (b) Ikegashira, K.; Nishihara, Y.; Hirabayashi, K.; Mori, A.; Hiyama, T. Copper(I) salt-promoted homo-coupling reaction of organosilanes. Chem. Commun. 1997, 1039-1040;
37. 2-TMEDA and its application for the solid-phase synthesis of bis-benzo[b]furan-linked 1,3-diynes. Org. Lett. 2003, 5, 909-912.
38. Coe, P. L.; Milner, N. E. Reactions of perfluoroalkylcoppper(I) compounds with acetylenes and halogenoacetylenes. J. Organomet. Chem. 1974, 70, 147-152.
39. 13C NMR of iodoalkynes. J. Am. Chem. Soc. 2002, 124, 370-371;
40. 13C NMR of iodoalkynes in Lewis basic solvents. J. Org. Chem. 2004, 69, 660-664.