Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

›› 2009, Vol. 17 ›› Issue (6): 1038-1042.

• • 上一篇

Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

白赢, 彭家建, 胡应乾, 厉嘉云, 邱化玉, 来国桥

Key Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China

收稿日期:2009-04-27 修回日期:2009-09-28 出版日期:2009-12-28 发布日期:2009-12-28
通讯作者: BAI Ying,E-mail:gqlai@hznu.edu.cn
基金资助:
Supported by the National High Technology Research and Development Program of China (2006AA03A134);Zhejiang Province Program (2008C14041)

Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

BAI Ying, PENG Jiajian, HU Yingqian, LI Jiayun, QIU Huayu, LAI Guoqiao

Key Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China

Received:2009-04-27 Revised:2009-09-28 Online:2009-12-28 Published:2009-12-28
Supported by:
Supported by the National High Technology Research and Development Program of China (2006AA03A134);Zhejiang Province Program (2008C14041)

摘要/Abstract

摘要： A series of aromatic acids has been tested as additives for the platinum-catalyzed hydrosilylation of styrene with triethoxysilane.Both excellent conversion of styrene and selectivity in favor of the β-adduct were achieved using aminobenzoic acids as additive.Moreover,the use of 4-aminobenzoic acid led to significantly superior enhancement in both catalytic activity and selectivity among the tested aminobenzoic acids.Indeed,100% conversion of styrene and 98.4% selectivity in favor of the β-adduct were obtained.Additionally,hydrosilylations of various alkenes with a variety of platinum catalysts have also been tested,and in each case the conversion of substrate and the selectivity of the β-adduct were promoted by using 4-aminobenzoic acid as additive.

关键词: hydrosilylation, platinum catalyst, aminoaromatic acid, additive

Abstract: A series of aromatic acids has been tested as additives for the platinum-catalyzed hydrosilylation of styrene with triethoxysilane.Both excellent conversion of styrene and selectivity in favor of the β-adduct were achieved using aminobenzoic acids as additive.Moreover,the use of 4-aminobenzoic acid led to significantly superior enhancement in both catalytic activity and selectivity among the tested aminobenzoic acids.Indeed,100% conversion of styrene and 98.4% selectivity in favor of the β-adduct were obtained.Additionally,hydrosilylations of various alkenes with a variety of platinum catalysts have also been tested,and in each case the conversion of substrate and the selectivity of the β-adduct were promoted by using 4-aminobenzoic acid as additive.

Key words: hydrosilylation, platinum catalyst, aminoaromatic acid, additive

白赢, 彭家建, 胡应乾, 厉嘉云, 邱化玉, 来国桥. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes[J]. , 2009, 17(6): 1038-1042.

BAI Ying, PENG Jiajian, HU Yingqian, LI Jiayun, QIU Huayu, LAI Guoqiao. Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes[J]. , 2009, 17(6): 1038-1042.

参考文献

1 Marciniec, B., Guliński, J., Urbaniak, W., Kornetka, Z.W., Comprehensive Handbook on Hydrosilylation, Pergamon Press, London(1992).
2 Sommer, L., Pietrusza, H.E.W., Whitmore, F.C., “Peroxide-catalyzed addition of trichlorosilane to 1-octene”, J. Am. Chem. Soc., 69(1), 188-189(1947).
3 Speier, J.L., Machay, F.P., Steward, Q.W., Campbell, P.G., “The addition of silicon hydrides to alkeneic double bonds(II) The use of group VIII metal catalysts”, J. Am. Chem. Soc., 79(4), 974-979(1957).
4 Ryan, J.W., Speier, J.L., “Notes-addition of silicon hydrides to alkeneic double bonds(IV) The addition to styrene and α-methylstyrene”, J.Org. Chem., 24(12), 2052-2053(1959).
5 Karstedt, B.D., Scotia, N.Y., “Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes”, US Pat., 3775452(1973).
6 Marciniec, B., Kornetka, Z.M., Urbaniak, W., “Platinum and rhodium complexes supported on aminated silica as hydrosilylation catalysts”, J. Mol. Catal., 12(2), 221-230(1981).
7 Wang, L.Z., Jiang, Y.Y., “Catalytic activity and selectivity of poly-γ-aminopropylsiloxane-Pt complex in hydrosilylation of unsaturated compounds”, Chin. J. Catal., 2(3), 236-238(1981).(in Chinese)
8 Wang, L.Z., Jiang, Y.Y., “An active and stable hydrosilylation catalyst, silica-poly-γ-mercaptopropyl-siloxane-platinum complex”, Macromol. Comm., 78-82(1983).(in Chinese)
9 Hu, C.Y., Han, X.M., Jiang, Y.Y., “Hydrosilylation of acetylene catalyzed by a sulfur-containing polysiloxane platinum complex”, J. Mol. Catal., 35(3), 329-333(1986).
10 Chen, Y.M., Lu, X.R., Zhong, Z.L., “Synthesis of poly-4,7dithianonylsesquisiloxane platinum complex and its catalyst activity on hydrosilylation of olefins with triethoxysilane”, Appl. Chem., 9(3), 26-30(1992).(in Chinese)
11 Liedtke, J., Loss, S., Widauer, C., Grützmacher, H., “Phosphiranes as ligands for platinum catalysed hydrosilylations”, Tetrahedron, 56, 143-156(2000).
12 Prignano, A.L., Trogler, W.C., “Silica-supported bis(trialkylphosphine) platinum oxalates. Photogenerated catalysts for hydrosilylation of alkenes”, J. Am. Chem. Soc., 109(12), 3586-3595(1987).
13 Yamamoto, K., Hayashi, T., Zembayashi, M., Kumada, M., “Catalytic asymmetric hydrosilylation of alkenes(II) chiral phosphine-platinum(II) complexes as hydrosilylation catalysts”, J. Organomet. Chem., 118(2), 161-181(1976).
14 Marciniec, B., Foltynowicz, Z., Urbaniak, W., “Catalysis of hydrosilylation(XV) A poly(phosphino-organosiloxanyl)silicate-supported rhodium(I) catalyst for gas-phase hydrosilylation of acetylene”, Appl. Organomet. Chem., 1(5), 459-463(1987).
15 Markó, I.E., Stérin, S., Buisine, O., Mignani, G., Branlard, P., Tinant, B., Declercq, J.P., “Selective and efficient platinum(0)-carbene complexes as hydrosilylation catalysts”, Science, 298, 204-206(2002).
16 Bo, D.G., Berthon-Gelloz, G., Tinant, B., “Hydrosilylation of alkynes mediated by N-heterocyclic carbene platinum(0) complexes”, Organometallics, 25(8), 1881-1890(2006).
17 Markó, I.E., Stérin, S., Buisine, O., Berthon, G., Michaud, G., Tinant, B., Declercq, J.P., “Highly active and selective platinum(0)-carbene complexes:Efficient, catalytic hydrosilylation of functionalised alkenes”, Adv. Synth. Catal., 346(12), 1429-1434(2004).
18 Berthon-Gelloz, G., Buisine, O., Brière, J. F., Michaud, G., Stérin, S., Mignani, G., Tinant, B., Declercq, J.P., Chapon, D., Markó, I.E., “Synthetic and structural studies of NHC-Pt(dvtms) complexes and their application as alkene hydrosilylation catalysts(NHC=N-heterocyclic carbene, dvtms=divinyltetramethylsiloxane)”, J. Organomet. Chem., 690(24/25), 6156-6168(2005).
19 Poyatos, M., Maisse-Francüois, A., Bellemin-Laponnaz, S., Gade, L.H., “Coordination chemistry of a modular N,C-chelating oxazole-carbene ligand and its applications in hydrosilylation catalysis”, Organometallics, 25(10), 2634-2641(2006).
20 Mehta, K.R., “Process for the preparation of siloxane-oxyalkylene copolymers”, US Pat., 4847398(1989).
21 Curtis, L., Schilling, Jr., “Method of highly efficient hydrosilylation”, CN 99122127.3(1999).
22 Hamze, A., Provot, O., Brion, J.D., Alami, M., “Xphos ligand and platinum catalysts:A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes”, J. Organomet. Chem., 693(16), 2789-2797(2008).
23 Hamze, A., Provot, O., Brion, J.D., Alami, M., “Platinum chloride/Xphos-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes”, Tetrahedron Lett., 49, 2429-2431(2008).
24 Arsenyan, P., Oberte, K., Rubina, K., Belyakov, S., “Synthesis and application of a new selenoplatinum catalyst”, Tetrahedron Lett., 46, 1001-1003(2005).

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Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

Effect of Aminoaromatic Acids as Additives on the Activity and Selectivity of the Platinum-catalyzed Hydrosilylation of Alkenes

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