以廉价的亚磷酸三乙酯为配体,首次用于Cu催化的碘代芳烃和末端炔烃的偶联反应,考察了不同Cu盐、金属纯度、碱和催化剂用量等条件对反应性能的影响.结果表明,当以高纯度的CuI (99.999％)为铜源,催化剂用量为5mol％时,在KOH作用下,该催化体系成功催化了一系列碘代芳烃和末端炔烃的反应,表现出良好的催化活性,此外,该催化体系还可用于2-苯基苯并呋喃的合成,为该类化合物的合成提供了一条较为经济的途径.
参考文献
| [1] | Chinchilla R;Nájera C .[J].Chemical Reviews,2007,107:874. |
| [2] | 邓维,刘磊,郭庆祥.铜催化交叉偶联反应研究的新进展[J].有机化学,2004(02):150-165. |
| [3] | Stephens R D;Castro C E .[J].Journal of Organic Chemistry,1963,28:3313. |
| [4] | Okuro K;Furuune M;Enna M;Miura M Nonura M .[J].Journal of Organic Chemistry,1993,58:4716. |
| [5] | Deng CL;Xie YX;Yin DL;Li JH .Copper(II) acetate/1,4-diphenyl-1,4-diazabuta-1,3-diene catalyzed Sonogashira cross-coupling of aryl halides with terminal alkynes under aerobic and solvent-free conditions[J].Synthesis: International Journal of Methods in Synthetic Organic Chemistry,2006(20):3370-3376. |
| [6] | Li J H;Li J L;Wang D P;Pi S F Xie Y X Zhang M B Hu X C .[J].Journal of Organic Chemistry,2006,72:2053. |
| [7] | Wang Y F;Deng W;Liu L;Guo Q X .[J].Chinese Chemical Letters,2005,16:1197. |
| [8] | Xie Y X;Deng C L;Pi S F;Li J H Yin D L .[J].Chinese Journal of Chemistry,2006,24:1290. |
| [9] | Tang B X;Wang F;Li J H;Xie Y X Zhang M B .[J].Journal of Organic Chemistry,2007,72:6294. |
| [10] | Guan J T;Yu G A;Chen L;Weng T Q Yuan J J Liu S H .[J].Applied Organometallic Chemistry,2009,23:75. |
| [11] | Lin, C.-H.;Wang, Y.-J.;Lee, C.-F. .Efficient copper-catalyzed cross-coupling reaction of alkynes with aryl iodides[J].European journal of organic chemistry,2010(23):4368-4371. |
| [12] | Wu MY;Mao JC;Guo J;Ji SJ .The use of a bifunctional copper catalyst in the cross-coupling reactions of aryl and heteroaryl halides with terminal alkynes[J].European journal of organic chemistry,2008(23):4050-4054. |
| [13] | Ma DW;Liu F .CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine[J].Chemical communications,2004(17):1934-1935. |
| [14] | Liu F;Ma DW .Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides[J].The Journal of Organic Chemistry,2007(13):4844-4850. |
| [15] | Mao J;Guo J;Ji S J .[J].Journal of Molecular Catalysis A:Chemical,2008,284:85. |
| [16] | Monnier F;Turtaut F;Duroure L;Taillefer M .Copper-catalyzed sonogashira-type reactions under mild palladium-free conditions[J].Organic letters,2008(15):3203-3206. |
| [17] | Klapars A.;Huang XH.;Buchwald SL. .A general and efficient copper catalyst for the amidation of aryl halides[J].Journal of the American Chemical Society,2002(25):7421-7428. |
| [18] | Gonda, Z.;Tolnai, G.L.;Novák, Z. .Dramatic impact of ppb levels of palladium on the "copper- catalyzed" sonogashira coupling[J].Chemistry: A European journal,2010(39):11822-11826. |
| [19] | Lauterbach, T.;Livendahl, M.;Rosellón, A.;Espinet, P.;Echavarren, A.M. .Unlikeliness of Pd-free gold(I)-catalyzed sonogashira coupling reactions[J].Organic letters,2010(13):3006-3009. |
| [20] | Bates C G;Saejueng P;Murphy J M;Venkataraman D .[J].Organic Letters,2002,4:4727. |
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