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Synthesis 2009(23): 4027-4031
DOI: 10.1055/s-0029-1217051
DOI: 10.1055/s-0029-1217051
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Simple One-Pot Procedure for the Direct Homocoupling of Terminal Alkynes Promoted by Copper Nanoparticles
Further Information
Received
28 May 2009
Publication Date:
19 October 2009 (online)
Publication History
Publication Date:
19 October 2009 (online)
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Abstract
The reaction of different terminal alkynes with readily prepared copper(0) nanoparticles led to the formation of the corresponding symmetrical 1,4-disubstituted 1,3-diynes in good yield. No palladium, ligands, or oxidant additives were needed. For aliphatic terminal alkynes, the use of sodium carbonate as base markedly improved the reaction rate and allowed the use of a substoichiometric amount of the copper nanoparticles.
Key words
copper nanoparticles - alkynes - dimerizations - coupling - 1,3-diynes
-
1a
Hunstman VD. In The Chemistry of the Carbon-Carbon Triple BondPatai S. Wiley-Interscience; London: 1978. p.553 -
1b
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632 -
1c
Sonogashira K. In Comprehensive Organic Synthesis Vol. 3:Trost BM. Pergamon Press; New York: 1991. p.551-561 -
1d
Rossi R.Carpita A.Bigelli C. Tetrahedron Lett. 1985, 26: 523 -
1e
Valenti E.Pericas MA.Serratosa F. J. Am. Chem. Soc. 1990, 112: 7405 -
1f
Liu G.Burton DJ. Tetrahedron Lett. 1997, 38: 4371 -
1g
Kitamura T.Lee CH.Taniguchi Y.Fujiwara Y. J. Am. Chem. Soc. 1997, 119: 619 -
2a
Nicolau KC.Zipkin RE.Dolle RE.Harris BD. J. Am. Chem. Soc. 1984, 106: 3548 -
2b
Crombie L.Hobbs AJW.Horsham MA.Blade RJ. Tetrahedron Lett. 1987, 28: 4875 -
2c
Holmes AB.Tabor AB.Baker R. J. Chem. Soc., Perkin Trans. 1 1991, 3307 -
2d
Hoye TR.Chanson P. Tetrahedron Lett. 1993, 34: 5043 -
2e
Nicolau KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490 -
3a
Stuüts A. Angew. Chem., Int. Ed. Engl. 1987, 26: 320 -
3b
Shi Shun ALK.Tykwinski RR. Angew. Chem. Int. Ed. 2006, 45: 1034 -
4a
Mayer SF.Steinreiber A.Orru RVA.Faber K. J. Org. Chem. 2002, 67: 9115 -
4b
Ratnayake AS.Hemscheidt T. Org. Lett. 2002, 4: 4667 -
4c
Yun H.Danishefsky SJ. J. Org. Chem. 2003, 68: 4519 - 5
Stefani HA.Costa IM.Zeni G. Tetrahedron Lett. 1999, 40: 9215 - 6
Zeni G.Panatieri RB.Lissner E.Menezes PH.Braga AL.Stefani HA. Org. Lett. 2001, 3: 819 -
7a
Babudri F.Colangiuli D.Di Lorenzo PA.Farinola GM.Omar OH.Naso F. Chem. Commun. 2003, 130 -
7b
Tour JM. Chem. Rev. 1996, 96: 537 -
7c
Bunz UHF.Rubin Y.Tobe Y. Chem. Soc. Rev. 1999, 28: 107 -
7d
Martin EE.Diederich F. Angew. Chem. Int. Ed. 1999, 38: 1351 -
7e
Diederich F.Rubin Y. Angew. Chem., Int. Ed. Engl. 1992, 31: 1101 -
7f
Mori A.Kondo T.Kato T.Nishihara Y. Chem. Lett. 2001, 286 -
7g
Tykwinski RR.Zhao Y. Synlett 2002, 1939 -
8a
Hoger S.Enkelmann V.Bonrad K.Tschierske C. Angew. Chem. Int. Ed. 2000, 39: 2268 -
8b
Ohkita M.Ando K.Suzuki T.Tsujim T. J. Org. Chem. 2000, 65: 4385 -
8c
Eisler S.Tykwinski RR. Angew. Chem. Int. Ed. 1999, 38: 1940 -
8d
Tobe Y.Fujii T.Matsumoto M.Naemura K.Achiba Y.Wakabayashi T. J. Am. Chem. Soc. 2000, 122: 1762 -
9a
de Meijere A.Kozhushkov S.Haumann T.Boese R.Puls C.Cooney MJ.Scott LT. Chem. Eur. J. 1995, 1: 124 -
9b
Campbell K.McDonald R.Branda NR.Tykwinski RR. Org. Lett. 2001, 3: 1045 -
9c
Campbell K.McDonald R.Tykwinski RR. J. Org. Chem. 2002, 67: 1133 -
10a
Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422 -
10b
Nicolau KC.Petasis NA.Zipkin RE.Uenishi J. J. Am. Chem. Soc. 1982, 104: 5555 ; and references cited therein -
10c
Yadav JS.Reddy BVS.Reddy KB.Gayathri KU.Prasad AR. Tetrahedron Lett. 2003, 44: 6493 -
11a
Eglinton G.Galbraith AR. J. Chem. Soc. 1959, 889 -
11b
Berscheid R.Voegtle F. Synthesis 1992, 58 -
12a
Hay AS. J. Org. Chem. 1962, 27: 3320 -
12b
Valenti E.Pericas MA.Serratosa F. J. Am. Chem. Soc. 1990, 112: 7405 -
12c
Liao Y.Fathi R.Yang Z. Org. Lett. 2003, 5: 909 - 13
Whitesides GM.Casey CP. J. Am. Chem. Soc. 1966, 88: 4541 -
14a
Lei A.Srivastava M.Zhang X. J. Org. Chem. 2002, 67: 1969 -
14b
Rossi R.Carpita A.Bigelli C. Tetrahedron Lett. 1985, 26: 523 -
14c
Vlasa M.Ciocan-Tarta I.Margineanu F.Oprean I. Tetrahedron 1996, 52: 1337 -
14d
Liu Q.Burton DJ. Tetrahedron Lett. 1997, 38: 4371 -
15a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 4467 -
15b
Kurita T.Abe M.Maegawa T.Monguchi Y.Sajiki H. Synlett 2007, 2521 -
15c
Shi M.Quian H.-X. Appl. Organomet. Chem. 2006, 20: 771 -
15d
Yan J.Wu J.Jin H. J. Organomet. Chem. 2007, 692: 3636 -
16a
Trost BM.Sorum MT.Cha C.Ruehter G. J. Am. Chem. Soc. 1997, 119: 698 -
16b
Lucking U.Pfaltz A. Synlett 2000, 1261 -
16c
Yang C.Nolan SP. J. Org. Chem. 2002, 67: 591 - 17
Batsanov AS.Collings JC.Fairlamb IJS.Holland JP.Howard JAK.Lin Z.Marder TB.Parsons AC.Ward RM.Zhu J. J. Org. Chem. 2005, 70: 703 - 18
Li J.-H.Liang Y.Zhang X.-D. Tetrahedron 2005, 61: 1903 -
19a
Li J.-H.Li J.-L.Wang D.-P.Pi S.-F.Xie Y.-X.Zhang M.-B.Hu X.-C. J. Org. Chem. 2007, 72: 2053 -
19b
Li J.-H.Li J.-L.Xie Y.-X. Synthesis 2007, 984 -
19c
Zhu BC.Jiang XZ. Appl. Organomet. Chem. 2007, 21: 345 - 20
Li D.Yin K.Li J.Jia X. Tetrahedron Lett. 2008, 49: 5918 - 21
Nishihara Y.Okamoto M.Inoue Y.Miyazaki M.Miyasaka M.Takagi K. Tetrahedron Lett. 2005, 46: 8661 - 22
Paixao MW.Weber M.Braga AL.de Azeredo JB.Deobald AM.Stefani HA. Tetrahedron Lett. 2008, 49: 2366 -
23a
Moreno-Mañas M.Pleixats R. Acc. Chem. Res. 2003, 36: 638 -
23b
Reetz MT.Lohmer G. Chem. Commun. 1996, 1921 -
23c
Reetz MT.Breinbauer R.Wanninger K. Tetrahedron Lett. 1996, 37: 4499 -
23d
Beller M.Fischer H.Kühlein K.Reisinger C.-P.Herrmann WA. J. Organomet. Chem. 1996, 520: 257 -
23e
Narayanan R.El-Sayed MA. J. Am. Chem. Soc. 2003, 125: 8340 -
23f
Reetz MT.de Vries JG. Chem. Commun. 2004, 1559 -
23g
Astruc D.Lu F.Aranzaes JR. Angew. Chem. Int. Ed. 2005, 44: 7852 - 24
Aiken JD.Finke RG. J. Mol. Catal. A: Chem. 1999, 145: 1 - For reduction reactions, see:
-
25a
Moglie Y.Alonso F.Vitale C.Yus M.Radivoy G. Appl. Catal., A 2006, 313: 94 -
25b
Moglie Y.Alonso F.Vitale C.Yus M.Radivoy G. Tetrahedron 2006, 62: 2812 -
25c
Radivoy G.Alonso F.Moglie Y.Vitale C.Yus M. Tetrahedron 2005, 61: 3859 -
25d
Alonso F.Moglie Y.Radivoy G.Vitale C.Yus M. Appl. Catal., A 2004, 271: 171 -
25e
Alonso F.Vitale C.Radivoy G.Yus M. Synthesis 2003, 443 - For coupling reactions, see:
-
25f
Moglie Y.Mascaró E.Nador F.Vitale C.Radivoy G. Synth. Commun. 2008, 38: 3861 -
25g
Moglie Y.Vitale C.Radivoy G. Tetrahedron Lett. 2008, 49: 1828 -
25h
Alonso F.Moglie Y.Radivoy G.Yus M. Tetrahedron Lett. 2009, 50: 2358 - 26
Brandsma L.Verkruijsse HD.Walda B. Synth. Commun. 1991, 21: 137 - 27
Moglie Y. Ph.D. Thesis Universidad Nacional del Sur; Argentina: 2008. - 28
Thathagar MB.Beckers J.Rothenberg G. Green Chem. 2004, 6: 215 - 29
Evano G.Blanchard N.Toumi M. Chem. Rev. 2008, 108: 3054 ; and references cited therein - 30
Perrin DD.Amarego WLF. Purification of Laboratory Chemicals Pergamon Press; Oxford: 1988. - 31
Cahiez G.Moyeux A.Buendia J.Duplais C. J. Am. Chem. Soc. 2007, 129: 13788 - 32
Li J.-H.Liang Y.Xie Y.-X. J. Org. Chem. 2005, 70: 4393