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在水相体系中,利用铜催化一系列氨基醇类底物(1.2 mmol)与碘代芳烃(1.0 mmol)进行N-芳基化反应.由于氨基醇具有双齿配位及相转移催化能力,该反应利用氨基醇类底物自身的促进作用,在不使用外加配体与相转移催化剂的温和条件下以高收率获得了氨基醇N-芳基化产物(64%-93%).

参考文献

[1] Belfield A J;Brown G R;Foubister A J .[J].Tetrahedron,1999,55:11399.
[2] Goodbrand H B;Hu N X .[J].Journal of Organic Chemistry,1999,64:670.
[3] Guo DL;Huang H;Xu JY;Jiang HL;Liu H .Efficient Iron-Catalyzed N-Arylation of Aryl Halides with Amines[J].Organic letters,2008(20):4513-4516.
[4] Feng Y S;Man Q S;Pan P;Pan Z Q Xu H J .[J].Tetrahedron Letters,2009,50:2585.
[5] Kwong F Y;Klapars A;Buchwald S L .[J].Organic Letters,2002,4:581.
[6] Taillefer M;Ouali A;Renard B;Spindler JF .Mild copper-catalyzed vinylation reactions of azoles and Phenols with vinyl bromides[J].Chemistry: A European journal,2006(20):5301-5313.
[7] Jiang DS;Fu H;Jiang YY;Zhao YF .CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature[J].The Journal of Organic Chemistry,2007(26):672-674.
[8] Martin R;Larsen CH;Cuenca A;Buchwald SL .Cu-catalyzed tandem C-N bond formation for the synthesis of pyrroles and heteroarylpyrroles[J].Organic letters,2007(17):3379-3382.
[9] Wagaw S;Buchwald S L .[J].Journal of Organic Chemistry,1996,61:7240.
[10] Barluenga J;Aznar F;Valdes C .[J].Angewandte Chemie International Edition,2004,43:343.
[11] Anderson K W;Tundel R E;Ikawa T;Altman R A,Buchwald S L .[J].Angewandte Chemie International Edition,2006,45:6523.
[12] Jones KL;Porzelle A;Hall A;Woodrow MD;Tomkinson NCO .Copper-catalyzed coupling of hydroxylamines with aryl iodides[J].Organic letters,2008(5):797-800.
[13] [J].化学学报,2012,33:1877.
[14] Antilla J C;Baskin J M;Barder T E;Buchwald S L .[J].Journal of Organic Chemistry,2004,69:5578.
[15] Zhu, LB;Li, GC;Luo, L;Guo, P;Lan, JB;You, JS .Highly Functional Group Tolerance in Copper-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles under Mild Conditions[J].The Journal of Organic Chemistry,2009(5):2200-2202.
[16] Lopezalvarado P.;Menendez JC.;Avendano C. .NEW SYNTHETIC APPLICATIONS OF ARYLLEAD TRIACETATES - N-ARYLATION OF AZOLES[J].The Journal of Organic Chemistry,1995(17):5678-5682.
[17] Kiyomori A.;Buchwald SL.;Marcoux JF. .An efficient copper-catalyzed coupling of aryl halides with imidazoles[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,1999(14):2657-2660.
[18] Klapars A;Antilla J C;Huang X H;Buchwald S L .[J].Journal of the American Chemical Society,2001,123:7727.
[19] Gujadhur R K;Bates C G;Venkataraman D .[J].Organic Letters,2001,3:4315.
[20] 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.
[21] Wu Z Q;Zhou L;Jiang Z Q;Wu D,Li Z K,Zhou X G.[J].EurJ Org Chem,2010:4971.
[22] Kwong F Y;Buchwald S L .[J].Organic Letters,2003,5:793.
[23] Cristau HJ;Cellier PP;Spindler JF;Taillefer M .Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides[J].Chemistry: A European journal,2004(22):5607-5622.
[24] Zhang, H;Cai, Q;Ma, DW .Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles[J].The Journal of Organic Chemistry,2005(13):5164-5173.
[25] Rao, HH;Fu, H;Jiang, YY;Zhao, YF .Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand[J].The Journal of Organic Chemistry,2005(20):8107-8109.
[26] Liu L B;Frohn M;Xi N;Dominguez C Hungate R Reider P J .[J].Journal of Organic Chemistry,2005,70:10135.
[27] Chen YJ;Chen HH .1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols[J].Organic letters,2006(24):5609-5612.
[28] Shafir A;Buchwald S L .[J].Journal of the American Chemical Society,2006,128:8742.
[29] Lü X;Bao W L .[J].Journal of Organic Chemistry,2007,72:3863.
[30] Yang M H;Liu F .[J].Journal of Organic Chemistry,2007,72:8969.
[31] Lu Z K;Twieg R J .[J].Tetrahedron Letters,2005,46:2997.
[32] Xu H J;Zheng F Y;Liang Y F;Cai Z Y Feng Y S Che D Q .[J].Tetrahedron Letters,2010,51:669.
[33] Jiao, J.;Zhang, X.-R.;Chang, N.-H.;Wang, J.;Wei, J.-F.;Shi, X.-Y.;Chen, Z.-G. .A facile and practical copper powder-catalyzed, organic solvent-and ligand-free ullmann amination of aryl halides[J].The Journal of Organic Chemistry,2011(4):1180-1183.
[34] Yong F F;Teo Y C;Tay S H;Tan B Y H Lim K H .[J].Tetrahedron Letters,2011,52:1161.
[35] Yin H Q;Jin M;Chen W;Chen C Zheng L K Wei P Han S Q .[J].Tetrahedron Letters,2012,53:1265.
[36] 张敬先,殷慧清,韩世清.水相中铜催化含氮杂环化合物的N-芳基化反应[J].有机化学,2012(08):1429-1433.
[37] Yang C T;Fu Y;Huang Y B;Yi J Guo Q X Liu L .[J].Angewandte Chemie International Edition,2009,48:7398.
[38] Chang J W W;Chee S;Mak S;Buranaprasertsuk P Chavasiri W Chan P W H .[J].Tetrahedron Letters,2008,49:2018.
[39] Shafir A;Lichtor P A;Buchwald S L .[J].Journal of the American Chemical Society,2007,129:3490.
[40] Marzaro G;Guiotto A;Chilin A .[J].Green Chemistry,2009,11:774.
[41] Li Y M;Wang H F;Jiang L L;Sun F F,Fu X M,Duan C Y.[J].EurJ Org Chem,2010:6967.
[42] Yu, H.-Z.;Jiang, Y.-Y.;Fu, Y.;Liu, L. .Alternative mechanistic explanation for ligand-dependent selectivities in copper-catalyzed N- and O-arylation reactions[J].Journal of the American Chemical Society,2010(51):18078-18091.
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