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化学进展 2017, Vol. 29 Issue (4): 412-425 DOI: 10.7536/PC161227 前一篇   后一篇

• 综述 •

N-杂环卡宾铂配合物的合成及其在有机反应中的应用

张凤香, 白赢*, 杨晓玲, 厉嘉云, 彭家建*   

  1. 杭州师范大学有机硅化学及材料技术教育部重点实验室 杭州 311121
  • 收稿日期:2016-12-16 修回日期:2017-01-17 出版日期:2017-04-15 发布日期:2017-03-31
  • 通讯作者: 白赢,e-mail:baiying0912@163.com;彭家建,e-mail:jjpeng@hznu.edu.cn E-mail:baiying0912@163.com;jjpeng@hznu.edu.cn
  • 基金资助:
    国家自然科学基金项目（No.21303034）和浙江省自然科学基金项目（No.LY14B030032）资助
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Synthesis of N-Heterocyclic Carbene Platinum Complexes and Application in the Organic Reaction

Fengxiang Zhang, Ying Bai*, Xiaoling Yang, Jiayun Li, Jiajian Peng*   

  1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China
  • Received:2016-12-16 Revised:2017-01-17 Online:2017-04-15 Published:2017-03-31
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No.21303034) and the Zhejiang Provincial Natural Science Foundation of China (No. LY14B030032).
N-杂环卡宾铂配合物作为催化剂广泛应用于诸多有机催化反应，表现出优良的催化性能及稳定的物理、化学性质，在一定程度上解决了传统催化剂使用过程中遇到的稳定性难题，是有机金属催化化学的研究热点之一。本文介绍了近年来N-杂环卡宾铂配合物的合成及其作为催化剂在不饱和化合物（烯烃、炔烃和酮等）硅氢加成反应、烯炔环异构化反应、烯烃氢胺化、烯烃硼化反应和炔烃水化反应等有机反应中的应用研究新成果和进展，分析了N-杂环卡宾铂配合物作为催化剂的催化机理和存在的不足，并对N-杂环卡宾铂配合物作为催化剂的应用前景进行了展望。
关键词： N-杂环卡宾铂, 催化, 应用
N-heterocyclic carbenes(NHC) have long been recognized as important ligands in organometallic chemistry, and NHC can form stable metal-carbon bonds with metals because of their stong σ-donating ability that provides the possibility to develop platinum NHC complexes as catalysts. N-heterocyclic carbene-platinum (Pt-NHC) complexes have been widely applied as catalysts in numerous catalytic organic reactions, in which the Pt-NHC system shows excellent catalytic performance and features with stable physical and chemical properties. On the other hand, the Pt-NHC complexes could be easily modified with different functional groups by modification of the stereo-effect and the corresponding electronic properties. In past years, it provides an effective method to solve the problem encountered in the process of using the traditional catalyst, and has become one of the hot topics in the organometallic chemistry and catalytic chemistry. In this manuscript, we summarize the recent progress in the synthesis of Pt-NHC complexes and their application in the catalytic organic transformations, including hydrosilylation of olefins/alkynes and ketones, isomerization reaction, hydroamination of unactivated olefins, borylation reactions of olefins, and hydration reaction of alkynes. Furthermore, the catalytic mechanism of all these reactions has been discussed. At last, the deficiencies as well as the perspective of Pt-NHC complexes have been also highlighted.

Contents
1 Introduction
2 Application of Pt-NHC complexes for hydrosilylation
2.1 Preparation of Pt(0)-NHC complexes and catalysis hydrosilylation
2.2 Preparation of Pt(Ⅱ)-NHC complexes and catalysis hydrosilylation
3 Application of Pt(Ⅱ)-NHC complexes in the cyclic-isomerization
4 Application of Pt(Ⅱ)-NHC complexes in the hydroamination of unactivated alkenes
5 Application of Pt(Ⅱ)-NHC complexes in the hydration of alkynes
6 Application of Pt(Ⅱ)-NHC complexes in the boride reaction of cycloolefin
7 Conclusion

Key words: N-heterocyclic carbene platinum, catalysis, application

中图分类号: 

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[1] Arduengo A J, Harlow R L, Kline M. J. Am. Chem. Soc., 1991, 113(1): 361.
[2] Herrmann W A. Angew. Chem., 2002, 114(8): 1342.
[3] Bourissou D, Guerret O, Gabbaï F P, Bertrand G. Chem. Rev., 2000, 100(1): 39.
[4] 钱延龙(Qian Y L), 陈新滋(Chen X Z). 金属有机化学与催化(Organometallic Chemistry and Catalysis). 北京:化学工业出版社(Beijing:Chemical Industry Press), 1997. 537.
[5] Peris E, Crabtree R H. Coord. Chem. Rev., 2004, 248 (21/24): 2239.
[6] Sommer W J, Weck M. Coord. Chem. Rev., 2007, 251(5/6): 860.
[7] Baker M V, Brown D H, Simpson P V, Skelton B W, White A H, Williams C C. J. Organomet. Chem., 2006, 691(26): 5485.
[8] Fortman G C, Nolan S P. Chem. Soc. Rev., 2011, 40: 5151.
[9] Velazquez H D, Verpoort F. Chem. Soc. Rev., 2012, 41: 7032.
[10] Corberan R, Mas-Marza E, Peris E. Eur. J. Inorg. Chem., 2009, (13): 1700.
[11] Poyatos M, Mata J A, Peris E. Chem. Rev., 2009, 109(8): 3677.
[12] Geier M, Gagne M R. J. Am. Chem. Soc., 2014, 136(8): 3032.
[13] Lersch M, Tilset M. Chem. Rev., 2005, 105(6): 2471.
[14] Field L D, Ward A. J. Organomet. Chem., 2003, 681(1/2): 91.
[15] Marciniec B, Guliński J. J. Organomet. Chem., 1983, 253(3): 349.
[16] Sommer L H, Pietrusza E W, Whitmore F C. J. Am. Chem. Soc., 1947, 69(1): 188.
[17] 白赢(Bai Y), 彭家建(Peng J J), 胡应乾(Hu Y Q), 厉嘉云(Li J Y), 来国桥(Lai G Q), 蒋剑雄(Jiang J X). 化学进展(Progress in Chemistry), 2009, (12): 2613.
[18] 厉嘉云(Li J Y), 彭家建(Peng J J), 李小年(Li X N), 马磊(Ma L), 白赢(Bai Y), 张国栋(Zhang G D), 来国桥(Lai G Q). 有机化学(Chinese Journal of Organic Chemistry), 2010, (10): 1468.
[19] Markó I E, Stérin S, Buisine O, Mignani G, Branlard P, Tinant B, Declercq J P. Science, 2002, 298: 204.
[20] Markó I E, Stérin S, Buisine O, Berthon G, Michaud G, Tinant B, Declercq J P. Adv. Synth. Catal., 2004, 346(12): 1429.
[21] Berthon-Gelloz G, Buisine O, Brière J F, Michaud G, Stérin S, Mignani G, Tinant B, Declercq J P, Chapon D, Markó I E. J. Organomet. Chem., 2005, 690(24/25): 6156.
[22] De Bo G, Berthon-Gelloz G, Tinant B, Markó I E. Organometallics, 2006, 25(10): 1881.
[23] Berthon-Gelloz G, Schumers J M, De Bo G, Markó I E. J. Org. Chem., 2008, 73(11): 4190.
[24] Sprengers J W, Mars M J, Duin M A, Cavel K J, Elsevier C J. J. Organomet. Chem., 2003, 679(2): 149.
[25] Dunsford J J, Cavell K J, Kariuki B. J. Organomet. Chem., 2011, 696(1): 188.
[26] Silbestri G F, Flores J C, Jesús E de. Organometallics, 2012, 31(17): 3355.
[27] Ruiz-Varilla A M, Baquero E A, Silbestri G F, Gonzalez-Arellano C, Jesús E de, Flores J C. Dalton Trans., 2015, (44): 18360.
[28] Dierick S, Markó I E. In eEROS Encyclopedia of Reagents for Organic Synthesis. Eds.: Paquette L A, Crich D, Fuchs P L, Molander G. Wiley. New York. 2013.
[29] Dierick S, Vercruysse E, Berthon-Gelloz G, Markó I E. Chem.-Eur. J., 2015, 21(1): 1.
[30] Meister T K, Kück J W, Riener K, Pöthig A, Herrmann W A, Kühn F E. J. Catal., 2016, 337(1): 157.
[31] Zhang Y, Zhao L, Patra P K, Ying J Y. Adv. Synth. Catal., 2008, 350: 662.
[32] Gribble G W. Chem. Soc. Rev., 1998, 27: 395.
[33] Pisiewicz S, Junge K, Beller M. Eur. J. Inorg. Chem., 2014, (14): 2345.
[34] Das S, Addis D, Zhou S, Junge K, Beller M. J. Am. Chem. Soc., 2010, 132(6): 1770.
[35] Das S, Join B, Junge K, Beller M. Chem. Commun., 2012, 48: 2683.
[36] Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem., Int. Ed., 2009, 48(50): 9507
[37] Hanada S, Tsutsumi E, Motoyama Y, Nagashima H. J. Am. Chem. Soc., 2009, 131(41): 15032.
[38] Poyatos M, Maisse-Franois A, Bellemin-Laponnaz S, Gade L H. Organometallics, 2006, 25(10): 2634.
[39] Hu J J, Li F, Hor T S A. Organomeallics, 2009, 28(4): 1212.
[40] Lu C X, Gu S J, Chen W Z, Qiu H Y. Dalton Trans., 2010, (39): 4198.
[41] Taige M A, Ahrens S, Strassner T. J. Organomet. Chem., 2011, 696(17): 2918.
[42] Munz D, Allolio C, Meyer D, Micksch M, Roessner L, Strassner T. J. Organomet. Chem., 2015, 794: 330.
[43] Bolbat E, Suarez-Alcantara K, Canton S E, Wendt O F. Inorg. Chim. Acta, 2016, 445: 129.
[44] Fürstner A. Chem. Soc. Rev., 2009, 38: 3208.
[45] Fürstner A, Szillat H, Stelzer F. J. Am. Chem. Soc., 2000, 122(28): 6785.
[46] Ferrer C, Raducan M, Nevado C, Claverie C K, Echavarren A M. Tetrahedron, 2007, 63(27): 6306.
[47] Blum J, Beer-Kraft H, Badrieh Y. J. Org. Chem., 1995, 60(17): 5567.
[48] Nieto-Oberhuber C, Munoz M P, Bunuel E, Nevado C, Cardenas D J, Echavarren A M. Angew. Chem., Int. Ed., 2004, 43(18): 2402.
[49] Kim S M, Park J H, Choi S Y, Chung Y K. Angew. Chem., Int. Ed., 2007, 46(32): 6172.
[50] Shibata T, Kobayash Y, Maekawa S, Toshida N, Takagi K. Tetrahedron, 2005, 61(38): 9018.
[51] Brissy D, Skander M, Retailleau P, Frison G, Marinetti A. Organometallics, 2009, 28(1): 140.
[52] Brissy D, Skander M, Retailleau P, Marinetti A. Organometallics, 2007, 26(24): 5782.
[53] Brissy D, Skander M, Retailleau P, Marinetti A. Org. Lett., 2009, 11(10): 2137.
[54] Jullien H, Brissy D, Sylvain R, Retailleau P, Naubron J V, Gladiali S, Marinetti A. Adv. Synth. Catal., 2011, 353(7): 1109.
[55] Zhang Y, Jullien H, Brissy D, Retailleau P, Voituriez A, Marinetti A. ChemCatChem, 2013, 5: 2051.
[56] Jung I G, Seo J, Lee S I, Choi S Y, Chung Y K. Organometallic, 2006, 25: 4240.
[57] Zhang Z, Lee S D. Widenhoefer R A. J. Am. Chem. Soc., 2009, 131(15): 5372.
[58] Cao P, Cabrera J, Padilla R, Serra D, Rominger F, Limbach M. Organometallics, 2012, 31(3): 921.
[59] Alonso F, Beletskaya I P, Yus M. Chem. Rev., 2004, 104(6): 3079.
[60] Hintermann L, Labonne A. Synthesis, 2007, 2007: 1121.
[61] Chatt J, Guy R G, Duncanson L A. J. Chem. Soc., 1961, 827.
[62] Hiscox W C, Jennings P W. Organometallics, 1990, 9(7): 1997.
[63] Hartman J W, Hiscox W C, Jennings P W. J. Org. Chem., 1993, 58(26): 7613.
[64] Jennings P W, Hartman J W, Hiscox W C. Inorg. Chim. Acta., 1994, 222(1/2): 317.
[65] Tokunaga M, Wakatsuki Y. Angew. Chem. Int. Ed., 1998, 37(20): 2867.
[66] Almássy A, Nagy C E, Bényei A C, Joó F. Organometallics, 2010, 29(11): 2484.
[67] Czégéni C E, Papp G, Kathó Á, Joó F. J. Mol. Catal. A: Chem., 2011, 340(1): 1.
[68] Baquero E A, Silbestri G F, Gómez-Sal P, Flores J C, Jesús de. Organometallics, 2013, 32(9): 2814.
[69] Miura T, Murakami M. Chem. Commun., 2007, 217.
[70] Pubill-Ulldemolins C, Bo C, Mata J A, Fernández E. Chem. Asian J., 2010, 5(1): 261.
[71] Lillo V, Mata J A, Segarra A M, Peris E, Fernandez E. Chem. Commun., 2007: 2184.
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