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Progress in Chemistry 2017, Vol. 29 Issue (4): 412-425 DOI: 10.7536/PC161227 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • 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).
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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

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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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