팔라듐 나노입자가 담지된 메조포러스 실리카의 제조와 이를 이용한 Suzuki Cross-Coupling 반응의 적용연구

김상욱; 주진; Sang-Wook Kim; Jin Joo

Clean Technology, Vol.17, No.1, 13-18, March, 2011

Synthesis of Palladium Nanoparticles Encapsulated in Phosphine Ligand-Grafted Mesoporous Silicas and Their Application to Suzuki Cross-Coupling Reaction

김상욱, 주진^{1, †}

아주대학교 분자과학기술학과, 443-749 경기도 수원시 영통구 원천동 산 5번지
¹경북대학교 응용화학과, 702-701 대구광역시 북구 산격동 1370번지

Sang-Wook Kim, and Jin Joo^{1, †}

Department of Molecular Science and Technology, Ajou University, Suwon 443-749, Korea
¹Department of Applied Chemistry, Kyungpook National University, Daegu, 702-701, Korea

E-mail:

초록

포스핀(phosphine) 리간드(ligand)가 도포된 메조포러스 실리카(mesoporous silicas)에 팔라듐 나노입자를 도입하여 새로운 팔라듐(Pd) 불균일 촉매(heterogeneous catalyst)를 제조하였다. 제조된 촉매는 브롬화벤젠 유도체(bromobenzene derivatives)들의 Suzuki cross-coupling 반응에 대하여 뛰어난 촉매활성을 나타내었고 촉매를 두 번째 사용하였을 때는 수율이 감소하였다.

Phosphine ligand-grafted mesoporous silica materials with large pores were prepared for the ligand-modified heterogeneous Pd nanocatalysts. New heterogeneous catalytic system was developed using palladium nanoparticJes encapsulated in phosphine ligand-grafted mesoporous silica. The catalyst showed good catalytic activities for Suzuki cross-coupling using bromobenzene derivatives due to excellent phosphinε ligand effects. Catalytic results showed nanoparticle catalysts can be rεcycled twice with decreased yields.

Keywords:Mesoporous silica;Pd nanoparticJcs;Suzuki cross-coupling reaction

[References]

Blaser H, Baiker A, Prins R, Heterogeneous Catalysis and Fine Chemicals IV, Elsevier, Amsterdam (1997)
Clark JH, Macquarrie DJ, Chem. Commun., 34(8), 853 (1998)
Baiker A, Curr. Opin. Solid State Mater. Sci., 3(1), 86 (1998)
Ertl G, Knozinger H, Weitkamp J, Handbook of Heterogeneous Catalysis, Wiley-VCH, Weinheim (1997)
Klingelhofer S, Heitz W, Greiner A, Oestreich S, Forster S, Antonietti M, J. Am. Chem. Soc., 119(42), 10116 (1997)
Mayer ABR, Mark JE, Morris RE, Polym. J., 30(3), 197 (1998)
Toshima N, Shiraishi Y, Teranishi T, Miyake M, Tominaga T, Watanabe H, Brijoux W, Bonnemann H, Schmid G, Appl. Organomet. Chem., 15(3), 178 (2001)
Bonnemann H, Brijoux W, Siepen K, Hormes J, Franke R, Pollmann J, Rothe J, Appl. Organomet. Chem., 11(10-11), 783 (1997)
Chen CW, Serizawa T, Akashi M, Chem. Mater., 11(5), 1381 (1999)
Gao HR, Angelici RJ, J. Am. Chem. Soc., 119(29), 6937 (1997)
Weddle KS, Aiken JD, Finke RG, J. Am. Chem. Soc., 120(23), 5653 (1998)
Reetz MT, Westermann E, Angew. Chem. Int. Ed., 39(1), 165 (2000)
Li Y, Hong XM, Collard DM, El-Sayed MA, Org. Lett., 2(15), 2385 (2000)
Kim SW, Son SU, Lee SS, Hyeon T, Chung YK, Chem. Commun., 37(21), 2212 (2001)
Son SU, Lee SI, Chung YK, Kim SW, Hyeon T, Org. Lett., 4(2), 277 (2002)
Kim W, Kim D, Hong Y, Kang T, Yi J, Clean Technol., 12(2), 107 (2006)
Jiang Y, Gao Q, J. Am. Chem. Soc., 128(3), 716 (2005)
Bedford RB, Singh UG, Walton RI, Williams RT, Davis SA, Chem. Mater., 17(4), 701 (2005)
Kim SS, Pauly TR, Pinnavaia TJ, Chem. Commun., 36(17), 1661 (2000)
Kim SW, Park J, Jang Y, Chung Y, Hwang S, Hyeon T, Nano Lett., 3(9), 1289 (2003)
Kim SW, Bae SJ, Hyeon T, Kim BM, Micropor. Mesopor. Mater., 44, 523 (2001)
Bae SJ, Kim SW, Hyeon T, Kim BM, Chem. Commun., 31, 32 (2000)
Miyaura N, Suzuki A, Chem. Rev., 95(7), 2457 (1995)
Suzuki A, J. Organomet. Chem., 576(1-2), 147 (1999)
Kim SW, Kim M, Lee WY, Hyeon T, J. Am. Chem. Soc., 124(26), 7642 (2002)
Sullivan JA, Flanagan KA, Hain H, Catal. Today., 145(1-2), 108 (2009)
Ellis PJ, Fairlamb IJS, Hackett SFJ, Wilson K, Lee AF, Angew. Chem. Int. Ed., 122(10), 1864 (2010)

[1] Blaser H, Baiker A, Prins R, Heterogeneous Catalysis and Fine Chemicals IV, Elsevier, Amsterdam (1997)

[2] Clark JH, Macquarrie DJ, Chem. Commun., 34(8), 853 (1998)

[3] Baiker A, Curr. Opin. Solid State Mater. Sci., 3(1), 86 (1998)

[4] Ertl G, Knozinger H, Weitkamp J, Handbook of Heterogeneous Catalysis, Wiley-VCH, Weinheim (1997)

[5] Klingelhofer S, Heitz W, Greiner A, Oestreich S, Forster S, Antonietti M, J. Am. Chem. Soc., 119(42), 10116 (1997)

[6] Mayer ABR, Mark JE, Morris RE, Polym. J., 30(3), 197 (1998)

[7] Toshima N, Shiraishi Y, Teranishi T, Miyake M, Tominaga T, Watanabe H, Brijoux W, Bonnemann H, Schmid G, Appl. Organomet. Chem., 15(3), 178 (2001)

[8] Bonnemann H, Brijoux W, Siepen K, Hormes J, Franke R, Pollmann J, Rothe J, Appl. Organomet. Chem., 11(10-11), 783 (1997)

[9] Chen CW, Serizawa T, Akashi M, Chem. Mater., 11(5), 1381 (1999)

[10] Gao HR, Angelici RJ, J. Am. Chem. Soc., 119(29), 6937 (1997)

[11] Weddle KS, Aiken JD, Finke RG, J. Am. Chem. Soc., 120(23), 5653 (1998)

[12] Reetz MT, Westermann E, Angew. Chem. Int. Ed., 39(1), 165 (2000)

[13] Li Y, Hong XM, Collard DM, El-Sayed MA, Org. Lett., 2(15), 2385 (2000)

[14] Kim SW, Son SU, Lee SS, Hyeon T, Chung YK, Chem. Commun., 37(21), 2212 (2001)

[15] Son SU, Lee SI, Chung YK, Kim SW, Hyeon T, Org. Lett., 4(2), 277 (2002)

[16] Kim W, Kim D, Hong Y, Kang T, Yi J, Clean Technol., 12(2), 107 (2006)

[17] Jiang Y, Gao Q, J. Am. Chem. Soc., 128(3), 716 (2005)

[18] Bedford RB, Singh UG, Walton RI, Williams RT, Davis SA, Chem. Mater., 17(4), 701 (2005)

[19] Kim SS, Pauly TR, Pinnavaia TJ, Chem. Commun., 36(17), 1661 (2000)

[20] Kim SW, Park J, Jang Y, Chung Y, Hwang S, Hyeon T, Nano Lett., 3(9), 1289 (2003)

[21] Kim SW, Bae SJ, Hyeon T, Kim BM, Micropor. Mesopor. Mater., 44, 523 (2001)

[22] Bae SJ, Kim SW, Hyeon T, Kim BM, Chem. Commun., 31, 32 (2000)

[23] Miyaura N, Suzuki A, Chem. Rev., 95(7), 2457 (1995)

[24] Suzuki A, J. Organomet. Chem., 576(1-2), 147 (1999)

[25] Kim SW, Kim M, Lee WY, Hyeon T, J. Am. Chem. Soc., 124(26), 7642 (2002)

[26] Sullivan JA, Flanagan KA, Hain H, Catal. Today., 145(1-2), 108 (2009)

[27] Ellis PJ, Fairlamb IJS, Hackett SFJ, Wilson K, Lee AF, Angew. Chem. Int. Ed., 122(10), 1864 (2010)