水溶性salen-Co（III）配合物催化的端炔水合反应

催化学报 , 2014, (10): 1695-1700. doi: 10.1016/S1872-2067(14)60105-4

水溶性salen-Co（III）配合物催化的端炔水合反应

王寿峰 ^1, , 苗成霞 ^2, , 王文芳 ^3, , 雷自强 ^4, , 孙伟 ^5,

1.西北师范大学化学化工学院，生态环境相关高分子材料教育部重点实验室，甘肃省高分子材料重点实验室，甘肃兰州730070; 中国科学院兰州化学物理研究所，羰基合成与选择氧化国家重点实验室，甘肃兰州730000

2.中国科学院兰州化学物理研究所，羰基合成与选择氧化国家重点实验室，甘肃兰州730000

3.中国科学院兰州化学物理研究所，羰基合成与选择氧化国家重点实验室，甘肃兰州730000

4.西北师范大学化学化工学院，生态环境相关高分子材料教育部重点实验室，甘肃省高分子材料重点实验室，甘肃兰州730070

5.中国科学院兰州化学物理研究所，羰基合成与选择氧化国家重点实验室，甘肃兰州730000

基金项目: 国家自然科学基金(21103207,21133011)@@@@This work was supported by the National Natural Science Foundation of China (21103207,21133011)

关键词：水合反应 , 炔烃 , 水溶性 , 钴 , 希夫碱配合物

Hydration of terminal alkynes catalyzed by a water-soluble salen-Co(III) complex

Keywords： Hydration , Alkynes , Water-solubility , Cobalt , Salen complex

报道了一种用于端炔水合反应的水溶性salen-Co(III)配合物催化剂，在使用硫酸作为共催化剂的条件下能高效得到产物甲基酮。该催化剂用量少，反应结束后可利用简单的萃取实现产物与催化剂分离，简化了后处理过程。此外，催化剂还可回收重复使用，但催化剂活性会略有下降。

A water-soluble salen-Co(III) complex was studied as catalyst for hydration of terminal alkynes to methyl ketones in the presence of H2SO4 as a co-catalyst. The products were obtained with excellent yields using relatively low catalyst loadings and a simple protocol. Notably, the products were easily separated from the catalyst after reaction by extraction, and the catalyst could be recovered and reused with only a slight loss of activity.

参考文献

[1]	Song F;Liu YM;Wang LL;Zhang HJ;He MY;Wu P .Highly selective synthesis of methyl ethyl ketone oxime through ammoximation over Ti-MWW[J].Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications,2007(1):22-31.
[2]	Hintermann L;Labonne A.[J].Synthesis,2007:1121.
[3]	Beller M;Seayad J;Tillack A;Jiao H J .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2004,43:3368.
[4]	Alonso F;Beletskaya I P;Yus M .[J].CHEMICAL REVIEWS,2004,104:3079.
[5]	Kutscheroff M .[J].Ber Dtsch Chem Ges,1884,17:13.
[6]	Kutscheroff M G .[J].Ber Dtsch Chem Ges,1909,42:2759.
[7]	Killian D B;Hennion G F;Nieuwland J A .[J].Journal of the American Chemical Society,1936,58:80.
[8]	Hiscox W;Jennings P W .[J].ORGANOMETALLICS,1990,9:1997.
[9]	Wu X F;Bezier D;DarcellC .[J].Advanced Synthesis and Catalysis,2009,351:367.
[10]	Cabrero-Antonino, J.R.;Leyva-Pérez, A.;Corma, A. .Regioselective hydration of alkynes by iron(III) Lewis/Br?nsted catalysis[J].Chemistry: A European journal,2012(35):11107-11114.
[11]	Fukuda Y;Shiragami H;Utimoto K;Nozaki H .[J].Journal of Organic Chemistry,1991,56:5816.
[12]	Hirabayashi T;Okirnoto Y;Saito A;Morita M;Sakaguchi S;Ishii Y .Iridium complex-catalyzed addition of water and alcohols to non-activated terminal alkynes[J].Tetrahedron,2006(10):2231-2234.
[13]	Thuong, M.B.T.;Mann, A.;Wagner, A. .Mild chemo-selective hydration of terminal alkynes catalysed by AgSbF _6[J].Chemical communications,2012(3):434-436.
[14]	Saha S;Sarbajna A;Bera J K .[J].Tetrahedron Letters,2014,55:1444.
[15]	Rao K T V;Prasad P S S;Lingaiah N .[J].Green Chemistry,2012,14:1507.
[16]	Corma A;Ruiz V R;Leyva-Prez A;Sabater M J .[J].Advanced Synthesis and Catalysis,2010,352:1701.
[17]	Marion, N;Ramon, RS;Nolan, SP .[(NHC)Au-I]-Catalyzed Acid-Free Alkyne Hydration at Part-per-Million Catalyst Loadings[J].Journal of the American Chemical Society,2009(2):448-449.
[18]	Mizushima E;Sato K;Hayashi T;Tanaka M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2002,41:4563.
[19]	Boeck, F.;Kribber, T.;Xiao, L.;Hintermann, L. .Mixed phosphane η~5-CpRuCl(PR_3)_2 complexes as ambifunctional catalysts for anti-markovnikov hydration of terminal alkynes[J].Journal of the American Chemical Society,2011(21):8138-8141.
[20]	Chevallier F;Breit B .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2006,45:1599.
[21]	Grotjahn D B;Lev D A .[J].Journal of the American Chemical Society,2004,126:12232.
[22]	Li, L.;Herzon, S.B. .Regioselective reductive hydration of alkynes to form branched or linear alcohols[J].Journal of the American Chemical Society,2012(42):17376-17379.
[23]	Li L;Herzon S B .[J].Nat Chem,2014,6:22.
[24]	Zeng M S;Li L;Herzon S B .[J].Journal of the American Chemical Society,2014,136:7058.
[25]	Tachinami, T.;Nishimura, T.;Ushimaru, R.;Noyori, R.;Naka, H. .Hydration of terminal alkynes catalyzed by water-soluble cobalt porphyrin complexes[J].Journal of the American Chemical Society,2013(1):50-53.
[26]	Xiong, DL;Wu, M;Wang, SF;Li, FW;Xia, CG;Sun, W .Synthesis of salan (salalen) ligands derived from binaphthol for titanium-catalyzed asymmetric epoxidation of olefins with aqueous H2O2[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2010(3):374-378.
[27]	Lv C W;Cheng Q G;Xu D Q;Wang S F Xia C G Sun W.[J].EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2011:3407.
[28]	Xiong D L;Hu X X;Wang S F;Miao C X Xia C G Sun W.[J].EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2011:4289.
[29]	Xu D Q;Wang S F;Shen Z Q;Xia C G Sun W .[J].Organic and Biological Chemistry,2012,10:2730.
[30]	Wang S F;Miao C X;Wang W F;Lei Z Q Sun W .[J].ChemCatChem,2014,6:1612.
[31]	Schaus SE.;Brandes BD.;Larrow JF.;Tokunaga M.;Hansen KB.;Gould AE. Furrow ME.;Jacobsen EN. .Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)Co-III complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols [Review][J].Journal of the American Chemical Society,2002(7):1307-1315.
[32]	Wu Z Q;Zhou Li;Jiang Z Q;Wu D Li Z K Zhou X G.[J].EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2010:4971.
[33]	Zhou N Z;Wang L;Thompson D W;Zhao Y M .[J].Tetrahedron,2011,67:125.
[34]	Teles JH.;Chabanas M.;Brode S. .Cationic gold(I) complexes: Highly efficient catalysts for the addition of alcohols to alkynes[J].Angewandte Chemie International Edition,1998(10):1415-1418.

上一张下一张

计量

下载量()
访问量()

作者相关

文章评分

您的评分：
1

0%
2

0%
3

0%
4

0%
5

0%

材料期刊网