基于借氢策略、醇为烷基化试剂的胺的N-烷基化反应是合成胺类化合物的绿色途径.在无外加氢源条件下,多相双金属Pt-Sn/γ-Al2O3催化剂可高效催化醇为烷基化试剂的伯(仲)胺的N-烷基化反应合成仲(叔)胺,反应副产物为水与极少量亚胺.催化体系的底物适应性好,目标产物收率高;催化剂可以循环使用,具有潜在的工业化应用前景.
参考文献
[1] | Brown B R.The Organic Chemistry of Aliphatic Nitrogen Compounds[M].New York:Oxford Univeristy Press,1994 |
[2] | Salvatore R N;Yoon C H;Jung K W .[J].Tetrahedron,2001,57:7785. |
[3] | 长谷川祥志;西村彻;广田敦史 .[P].CN 101 331 109,2008. |
[4] | Hamid MHSA;Slatford PA;Williams JMJ .Borrowing hydrogen in the activation of alcohols[J].Advanced synthesis & catalysis,2007(10):1555-1575. |
[5] | Watson A J A;Williams J M J .[J].Science,2010,329:635. |
[6] | Guillena G;Ramón D J;Yus M .[J].Chemical Reviews,2010,110:1611. |
[7] | Suzuki, T. .Organic synthesis involving iridium-catalyzed oxidation[J].Chemical Reviews,2011(3):1825-1845. |
[8] | Hamid M H S A;Williams J M J .[J].Tetrahedron Letters,2007,48:8263. |
[9] | Grigg R;Mitchell T R B;Sutthivaiyakit S;Tongpenyai T.[J].Journal of the Chemical Society,Chemical Communications,1981:611. |
[10] | Watanabe Y;Tsuji Y;Ohsugi Y .[J].Tetrahedron Letters,1981,22:2667. |
[11] | Fujita K;Li Z;Ozeki N;Yamaguchi R .[J].Tetrahedron Letters,2003,44:2687. |
[12] | Fujita K-I;Yamaguchi R .[J].Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry,2005,4:560. |
[13] | Fujita K-I;Enoki Y;Yamaguchi R .[J].Organic Syntheses,2006,83:217. |
[14] | Fujita KI;Enoki Y;Yamaguchi R .Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines[J].Tetrahedron,2008(8):1943-1954. |
[15] | Yamaguchi R;Kawagoe S;Asai C;Fujita KI .Selective synthesis of secondary and tertiary amines by Cp*iridium-catalyzed multialkylation of ammonium salts with alcohols[J].Organic letters,2008(2):181-184. |
[16] | Tillack A;Hollmann D;Michalik D;Beller M .[J].Tetrahedron Letters,2006,47:8881. |
[17] | Hollmann D;Tillack A;Michalik D;Jackstell R;Beller M .An improved ruthenium catalyst for the environmentally benign amination of primary and secondary alcohols[J].Chemistry, an Asian journal,2007(3):403-410. |
[18] | B(a)hn S;Imm S;Mevius K;Neubert L Tillack A Williams J M J Beller M .[J].Chemistry-A European Journal,2010,16:3590. |
[19] | Hamid MHSA;Williams JMJ .Ruthenium catalysed N-alkylation of amines with alcohols[J].Chemical communications,2007(7):725-727. |
[20] | Hamid, MHSA;Allen, CL;Lamb, GW;Maxwell, AC;Maytum, HC;Watson, AJA;Williams, JMJ .Ruthenium-Catalyzed N-Alkylation of Amines and Sulfonamides Using Borrowing Hydrogen Methodology[J].Journal of the American Chemical Society,2009(5):1766-1774. |
[21] | Saidi, O;Blacker, AJ;Farah, MM;Marsden, SP;Williams, JMJ .Iridium-catalysed amine alkylation with alcohols in water[J].Chemical communications,2010(9):1541-1543. |
[22] | Waston A J A;Maxwell A C;Williams J M J .[J].Journal of Organic Chemistry,2011,76:2328. |
[23] | Shi F;Tse M K;Cui X J;G(o)rdes D,Michalik D,Thurow K,Deng Y Q,Beller M .[J].Angewandte Chemie International Edition,2009,48:5912. |
[24] | Fratt E F;Frazza E J .[J].Journal of the American Chemical Society,1954,76:6174. |
[25] | He J L;Kim J W;Yamaguchi K;Mizuno N .[J].Angewandte Chemie International Edition,2009,48:9888. |
[26] | Yamaguchi, K.;He, J.;Oishi, T.;Mizuno, N. .The "borrowing hydrogen strategy" by supported ruthenium hydroxide catalysts: Synthetic scope of symmetrically and unsymmetrically substituted amines[J].Chemistry: A European journal,2010(24):7199-7207. |
[27] | Shi F;Tse M K;Pohl M-M;Brückner A,Zhang S,Beller M .[J].Angewandte Chemie International Edition,2007,46:8866. |
[28] | Shi, F;Tse, MK;Zhou, SL;Pohl, MM;Radnik, J;Hubner, S;Jahnisch, K;Bruckner, A;Beller, M .Green and Efficient Synthesis of Sulfonamides Catalyzed by Nano-Ru/Fe3O4[J].Journal of the American Chemical Society,2009(5):1775-1779. |
[29] | Zhang Y;Qi X J;Cui X J;Shi F Deng Y Q .[J].Tetrahedron Letters,2011,52:1334. |
[30] | Cui X J;Zhang Y;Shi F;Deng Y Q .[J].Chemistry-A European Journal,2011,17:1021. |
[31] | Cui X J;Shi F;Tse M K;G(o)rdes D Thurow K Beller M Deng Y Q .[J].Advanced Synthesis and Catalysis,2009,351:2949. |
[32] | Sun H;Su F Z;Ni J;Cao Y,He H Y,Fan K N .[J].Angewandte Chemie International Edition,2009,4g:4390. |
[33] | He L;Wang L C;Sun H;Ni J,Cao Y,He H Y,Fan K N .[J].Angewandte Chemie International Edition,2009,4g:9538. |
[34] | He, L.;Lou, X.-B.;Ni, J.;Liu, Y.-M.;Cao, Y.;He, H.-Y.;Fan, K.-N. .Efficient and clean gold-catalyzed one-pot selective n-alkylation of amines with alcohols[J].Chemistry: A European journal,2010(47):13965-13969. |
[35] | Lou X B;He L;Qian Y;Liu Y M Cao Y Fan K N .[J].Advanced Synthesis and Catalysis,2011,353:281. |
[36] | Tang, C.-H.;He, L.;Liu, Y.-M.;Cao, Y.;He, H.-Y.;Fan, K.-N. .Direct one-pot reductive N-alkylation of nitroarenes by using alcohols with supported gold catalysts[J].Chemistry: A European journal,2011(26):7172-7177. |
[37] | He, W.;Wang, L.;Sun, C.;Wu, K.;He, S.;Chen, J.;Wu, P.;Yu, Z. .Pt-Sn/γ-Al_2O_3-catalyzed highly efficient direct synthesis of secondary and tertiary amines and imines[J].Chemistry: A European journal,2011(47):13308-13317. |
[38] | Wang L D;He W;Wu K K;He S B Sun C L Yu Z K .[J].Tetrahedron Letters,2011,52:7103. |
[39] | 何松波,赖玉龙,毕文君,杨旭,荣欣,孙承林.K助剂对Pt-Sn-K/γ-Al_2O_3催化剂上C_(16)正构烷烃脱氢反应的影响[J].催化学报,2010(04):435-440. |
[40] | He S B;Sun C L;Bai Z W;Dai X H Wang B .[J].Applied Catalysis A:General,2009,356:88. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%