Applications of Metal Nanopore Catalysts in Organic Synthesis

This account is dedicated to the memory of Professor Manfred Schlosser for his outstanding contributions to organometallic chemistry.

Abstract

Reducing the size of bulk metals to nanometer scale can result in the display of extraordinary physical and chemical properties. Typically, metal nanoparticles (MNPs) are prepared from metal atoms or metal salts and show remarkable catalytic properties. Metal nanopores (MNPores) are prepared through a totally reverse approach (from bulk metal to nanosized metal): alloy M¹M² is fabricated from metal M¹ and metal M², and then dealloying of M² results in a nanoporous framework of metal M¹. This account summarizes MNPore-catalyzed reactions developed in our group, and their comparison with other representative catalytic reactions.

1 Introduction

1.1 Fabrication and Structural Characteristics of Nanoporous Gold

2 Oxidation Reactions

2.1 Oxidation of Alcohols

2.2 Synthesis of Formamides Through Oxidative Coupling of Methanol with Amines

2.3 Oxidation of Silanes

3 Reduction Reactions

3.1 Semihydrogenation of Alkynes

3.2 Reduction of Quinoline

3.3 Reduction of Imines and Reductive Amination of Carbonyls

3.4 Reduction of α,β-Unsaturated Aldehydes

3.5 1,4-Hydrosilylation of Cyclic Enones

4 Formation of C–Si, C–B, and C–C Bonds Using Alkynes

4.1 Hydrosilylation of Alkynes

4.2 Diboration of Alkynes

4.3 Benzannulation Reaction

5 CuNPore-Catalyzed Click Reaction

6 Suzuki, Negishi and Heck Coupling Reactions

7 Concluding Remarks

Key words

metal nanoparticle catalysts - metal nanopore catalysts - nanoparticles - nanopores - heterogeneous - homogeneous - oxidation - reduction

• References

• 1a Zielasek V, Jurgens B, Schulz C, Biener J, Biener MM, Hamza AV. Angew. Chem. Int. Ed. 2006; 45: 8241
• 1b Xu CX, Su JX, Xu XH, Liu PP, Zhao HJ, Tian F, Ding Y. J. Am. Chem. Soc. 2007; 129: 42
• 1c Asao N, Jin T, Tanaka S, Yamamoto Y. Pure Appl. Chem. 2012; 84: 1771
• 2 Vanýsek P. Electrochemical Series . In Handbook of Chemistry and Physics . Haynes WM. CRC Press; Boca Raton: 2012: 93rd ed., 5-80
• 3 Parida S, Kramer D, Volkert CA, Rosner H, Erlebacher J, Weissmuller J. Phys. Rev. Lett. 2006; 97: 035504
• 4 Petegem SV, Brandstetter S, Maass R, Hodge AM, El-Dasher BS, Biener J, Schmitt B, Borca C, Swygenhoven HV. Nano Lett. 2009; 9: 1158
• 5a Fujita T, Guan P, McKenna K, Lang X, Hirata A, Zhang L, Tokunaga T, Arai S, Yamamoto Y, Tanaka N, Ishikawa Y, Asao N, Yamamoto Y, Erlebacher J, Chen M. Nat. Mater. 2012; 11: 775
• 5b Yan M, Jin T, Ishikawa Y, Minato T, Fujita T, Chen L.-Y, Bao M, Asao N, Chen M, Yamamoto Y. J. Am. Chem. Soc. 2012; 134: 17536
• 6 Hvolbæk B, Janssens TV. W, Clausen BS, Falsig H, Christensen CH, Nørskov JK. Nano Today 2007; 2: 14
• 7a Lemire C, Meyer R, Shaikhutdinov S, Freund H.-J. Angew. Chem. Int. Ed. 2003; 43: 118
• 7b Lopez N, Janssens TV. W, Clausen BS, Xu Y, Mavrikakis M, Bligaard T, Nørskov JK. J. Catal. 2004; 223: 232
• 7c Molina LM, Hammer B. Phys. Rev. B 2004; 69: 155424
• 8a Haruta M, Kobayashi T, Sano H, Yamada N. Chem. Lett. 1987; 16: 405
• 8b Haruta M, Yamada N, Kobayashi T, Iijima S. J. Catal. 1989; 115: 301
• 8c Haruta M. Catal. Today 1997; 36: 153
• 9a Della Pina C, Falletta E, Prati L, Rossi M. Chem. Soc. Rev. 2008; 37: 2077
• 9b Della Pina C, Falletta E. Catal. Sci. Technol. 2011; 1: 1564
• 9c Tsukuda T, Tsunoyama H, Sakurai H. Chem. Asian J. 2011; 6: 736
• 9d Della Pina C, Falletta E, Rossi M. Chem. Soc. Rev. 2012; 41: 350
• 9e Zhang Y, Cui X, Shi F, Deng Y. Chem. Rev. 2012; 112: 2467
• 10a Wittstock A, Zielasek V, Biener J, Friend CM, Bäumer M. Science 2010; 327: 319
• 10b Takale BS, Bao M, Yamamoto Y. Org. Biomol. Chem. 2014; 12: 2005
• 10c Takale BS, Bao M, Yamamoto Y. Nanoporous Metals as Novel Catalysts for Chemical Transformations. In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier; Waltham, MA: 2015.
• 11 Cainelli G, Cardillo G. Chromium Oxidations in Organic Chemistry. 1984
• 12 Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
• 13a Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
• 13b Zhdankin VV. J. Org. Chem. 2011; 76: 1185
• 14a Richardson RD, Wirth T. Angew. Chem. Int. Ed. 2006; 45: 4402
• 14b Ochiai M, Miyamoto K. Eur. J. Org. Chem. 2008; 4229
• 15 Sheldon RA, Arends IW. C. E, Dijksman A. Catal. Today 2000; 57: 157
• 16 Naota T, Takaya H, Murahashi S.-I. Chem. Rev. 1998; 98: 2599
• 17 Barak G, Dakka J, Sasson Y. J. Org. Chem. 1988; 53: 3553
• 18 Farmer V, Welton T. Green Chem. 2002; 4: 97
• 19 Ma CY, Dou BJ, Li JJ, Cheng J, Hu Q, Hao ZP, Qiao SZ. Appl. Catal., B 2009; 92: 202
• 20 Hu J, Chen L, Zhu K, Suchopar A, Richards R. Catal. Today 2007; 122: 277
• 21 Liu YM, Tsunoyama H, Akita T, Tsukuda T. J. Phys. Chem. C 2009; 113: 13457
• 22 Asao N, Hatakeyama N, Menggenbateer; Minato T, Ito E, Hara M, Kim Y, Yamamoto Y, Chen M, Zhang W, Inoue A. Chem. Commun. 2012; 48: 4540
• 23 Gunanathan C, Ben-David Y, Milstein D. Science 2007; 317: 790
• 24 Nordstrøm LU, Vogt H, Madsen R. J. Am. Chem. Soc. 2008; 130: 17672
• 25 Zhang Y, Chen C, Ghosh SC, Li Y, Hong SH. Organometallics 2010; 29: 1374
• 26 Shimizu K, Ohshima K, Satsuma A. Chem. Eur. J. 2009; 15: 9977
• 27 Geukens I, Vermoortele F, Meledina M, Turner S, Van Tendeloo G, De Vos DE. Appl. Catal., A 2014; 469: 373
• 28 Zhu J, Zhang Y, Shi F, Deng Y. Tetrahedron Lett. 2012; 53: 3178
• 29 Preedasuriyachai P, Kitahara H, Chavasiri W, Sakurai H. Chem. Lett. 2010; 39: 1174
• 30 Soule JF, Miyamura H, Kobayashi S. J. Am. Chem. Soc. 2011; 133: 18550
• 31 Tanaka S, Minato T, Ito E, Hara M, Kim Y, Yamamoto Y, Asao N. Chem. Eur. J. 2013; 19: 11832
• 32a Ojima I, Li Z, Zhu J In The Chemistry of Organic Silicon Compounds . Rappoport S, Apeloig Y. Wiley; New York: 1998. Chap. 29
• 32b Chandrasekhar V, Boomishankar R, Nagendran S. Chem. Rev. 2004; 104: 5847
• 32c Lickiss PD. Adv. Inorg. Chem. 1995; 42: 147
• 33 Schubert U, Lorenz C. Inorg. Chem. 1997; 36: 1258
• 34 Lee Y, Seomoon D, Kim S, Han H, Chang S, Lee PH. J. Org. Chem. 2004; 69: 1741
• 35 Ison EA, Corbin RA, Abu-Omar MM. J. Am. Chem. Soc. 2005; 127: 11938
• 36a Mori K, Tano M, Mizugaki T, Ebitani K, Kaneda K. New J. Chem. 2002; 26: 1536
• 36b Mitsudome T, Arita S, Mori H, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2008; 47: 7938
• 36c Mitsudome T, Noujima A, Mizugaki T, Jitsukawa K, Kaneda K. Chem. Commun. 2009; 5302
• 37 John J, Gravel E, Hagge A, Li H, Gacoin T, Doris E. Angew. Chem. Int. Ed. 2011; 50: 7533
• 38 Chauhan BP. S, Sarkar A, Chauhan M, Roka A. Appl. Organomet. Chem. 2009; 23: 385
• 39 Asao N, Ishikawa Y, Hatakeyama N, Menggenbateer; Yamamoto Y, Chen M, Zhang W, Inoue A. Angew. Chem. Int. Ed. 2010; 49: 10093
• 40 Li Z, Zhang C, Tian J, Zhang Z, Zhang X, Ding Y. Catal. Commun. 2014; 53: 53
• 41a Lindlar H. Helv. Chim. Acta 1952; 35: 446
• 41b Lindlar H, Dubuis R. Org. Synth. 1966; 46: 89
• 41c Chandrasekhar S, Narsihmulu C, Chandrashekar G, Shyamsunder T. Tetrahedron Lett. 2004; 45: 2421
• 42 Li J, Hua R. Chem. Eur. J. 2011; 17: 8462
• 43 Whittaker AM, Lalic G. Org. Lett. 2013; 15: 1112
• 44 Alonso F, Osante I, Yus M. Tetrahedron 2007; 63: 93
• 45 Hori J, Murata K, Sugai T, Shinohara H, Noyori R, Arai N, Kurono N, Ohkuma T. Adv. Synth. Catal. 2009; 351: 3143
• 46 Li S.-S, Liu X, Liu Y.-M, He H.-Y, Fan K.-N, Cao Y. Chem. Commun. 2014; 50: 5626
• 47 Vasilikogiannaki E, Titilas I, Vassilikogiannakis G, Stratakis M. Chem. Commun. 2015; 51: 2384
• 48 Mitsudome T, Takahashi Y, Ichikawa S, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2013; 52: 1481
• 49 Li G, Jin R. J. Am. Chem. Soc. 2014; 136: 11347
• 50 Wagh YS, Asao N. J. Org. Chem. 2015; 80: 847
• 51 Katritzky AR, Stanislaw R, Rachwal B. Tetrahedron 1996; 52: 15031
• 52 Dobereiner GE, Nova A, Schley ND, Hazari N, Miller SJ, Eisenstein O, Crabtree RH. J. Am. Chem. Soc. 2011; 133: 7547
• 53 Rueping M, Koenigs RM, Borrmann R, Zoller J, Weirich TE, Mayer J. Chem. Mater. 2011; 23: 2008
• 54 Hashimoto N, Takahashi Y, Hara T, Shimazu S, Mitsudome T, Mizugaki T, Jitsukawa K, Kaneda K. Chem. Lett. 2010; 39: 832
• 55 Ren D, He L, Yu L, Ding R.-S, Liu Y.-M, Cao Y, He H.-Y, Fan K.-N. J. Am. Chem. Soc. 2012; 134: 17592
• 56 Yan M, Jin T, Chen Q, Ho EH, Fujita T, Chen L.-Y, Bao M, Chen M, Asao N, Yamamoto Y. Org. Lett. 2013; 15: 1484
• 57 Abdel-Magid AF, Mehrman SJ. Org. Proc. Res. Dev. 2006; 10: 971
• 58 Saxena I, Borah R, Sarma JC. J. Chem. Soc., Perkin Trans. 1 2000; 503
• 59 Aida T, Kuboki N, Kato K, Uchikawa W, Matsuno C, Okamoto S. Tetrahedron Lett. 2005; 46: 1667
• 60 Moglie Y, Alonso F, Vitale C, Yus M, Radivoy G. Tetrahedron 2006; 62: 2812
• 61 Tararov VI, Kadyrov R, Riermeier TH, Dingerdissen U, Börner A. Org. Prep. Proced. Int. 2004; 36: 99
• 62 Lei Q, Wei Y, Talwar D, Wang C, Xue D, Xiao J. Chem. Eur. J. 2013; 19: 4021
• 63 Bhor MD, Bhanushali MJ, Nandurkar NS, Bhanage BM. Tetrahedron Lett. 2008; 49: 965
• 64 Kumar NU, Sudhakar Reddy B, Prabhakar Reddy V, Bandichhor R. Tetrahedron Lett. 2012; 53: 4354
• 65 Cho BT, Kang SK. Tetrahedron 2005; 61: 5725
• 66 Misumi Y, Seino H, Mizobe Y. J. Am. Chem. Soc. 2009; 131: 14636
• 67 Mirza-Aghayan M, Tavana MM, Rahimifard M, Boukherroub R. Appl. Organomet. Chem. 2014; 28: 113
• 68 Nasrollahzadeh M. New J. Chem. 2014; 38: 5544
• 69 Takale BS, Tao SM, Yu XQ, Feng XJ, Jin T, Bao M, Yamamoto Y. Org. Lett. 2014; 16: 2558
• 70 Takale BS, Tao SM, Yu XQ, Feng XJ, Jin T, Bao M, Yamamoto Y. Tetrahedron 2015;
• 71a Mäki-Arvela P, Hájek J, Murzin DY. Appl. Catal., A 2005; 292: 1
• 71b Gallezot P, Richard D. Catal. Rev. Sci. Eng. 1998; 40: 81
• 71c Singh UK, Vannice MA. Appl. Catal., A 2001; 213: 1
• 72 Ramos-Fernández EV, Ruiz-Martínez J, Serrano-Ruiz JC, Silvestre-Albero J, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Appl. Catal. A 2011; 402: 50
• 73 Pournara A, Kovala-Demertzi D, Kourkoumelis N, Georgakopoulos S, Kostas ID. Catal. Commun. 2014; 43: 57
• 74 Raj KJ. A, Prakash M, Elangovan T, Viswanathan B. Catal. Lett. 2012; 142: 87
• 75 Qi X, Rosa Axet M, Philippot K, Lecante P, Serp P. Dalton Trans. 2014; 43: 9283
• 76 Shibata M, Kwata N, Masumoto T, Kimura H. J. Chem. Soc., Chem. Commun. 1988; 154
• 77 Bailie JE, Hutchings GJ. Chem. Commun. 1999; 2151
• 78 Milone C, Crisafulli C, Ingoglia R, Schipilliti L, Galvagno S. Catal Today 2007; 122: 341
• 79 Wang M.-M, He L, Liu Y.-M, Cao Y, He HY, Fan K.-N. Green Chem. 2011; 13: 602
• 80 Shi H, Xu N, Zhao D, Xu B.-Q. Catal. Commun. 2008; 9: 1949
• 81 Takale BS, Wang S, Zhang X, Feng X, Yu X, Jin T, Bao M, Yamamoto Y. Chem. Commun. 2014; 50: 14401
• 82 Rasmussen JK. Synthesis 1977; 91
• 83 Mahoney WS, Brestensky DM, Stryker JM. J. Am. Chem. Soc. 1988; 110: 293
• 84 Blackwell JM, Morrison DJ, Piers WE. Tetrahedron 2002; 58: 8247
• 85 Benohoud M, Tuokko S, Pihko PM. Chem. Eur. J. 2011; 17: 8404
• 86 Tuokko S, Pihko PM. Org. Process Res. Dev. 2014; 18: 1740
• 87 Chen Q, Tanaka S, Fujita T, Chen L, Minato T, Ishikawa Y, Chen M, Asao N, Yamamoto Y, Jin T. Chem. Commun. 2014; 50: 3344
• 88a Marciniec B, Gulinky J, Urbaniak W, Kornetka ZW In Comprehensive Handbook on Hydrosilylation . Marciniec B. Pergamon Press; Oxford: 1992
• 88b Marciniec B. Hydrosilylation and Related Reactions of Silicon Compounds. In Applied Homogeneous Catalysis with Organometallic Compounds . Cornilis B, Hermann WA. Wiley-VCH; Weinheim: 1996. Chapter 2.6
• 89 Guo W, Pleixats R, Shafir A, Parella T. Adv. Synth. Catal. 2015; 357: 89
• 90 Pascu O, Liautard V, Vaultier M, Pucheault M, Aymonier C. RSC Adv. 2014; 4: 59953
• 91 Cano R, Yus M, Ramón DJ. ACS Catal. 2012; 2: 1070
• 92 Alonso F, Buitrago R, Moglie Y, Ruiz-Martínez J, Sepúlveda-Escribano A, Yus M. J. Organomet. Chem. 2011; 696: 368
• 93 Caporusso AM, Aronica LA, Schiavi E, Martra G, Vitulli G, Salvadori P. J. Organomet. Chem. 2005; 690: 1063
• 94 Aronica LA, Schiavi E, Evangelisti C, Caporusso AM, Salvadori P, Vitulli G, Bertinetti L, Martra G. J. Catal. 2009; 266: 250
• 95 Ishikawa Y, Yamamoto Y, Asao N. Catal. Sci. Technol. 2013; 3: 2902
• 96a Muetterties EL. The Chemistry of Boron and its Compounds . Wiley; New York: 1967: 398-399
• 96b Onak T. Organoborane Chemistry . Academic Press; New York: 1975: 38-40
• 96c Takaya J, Iwasawa N. ACS Catal. 2012; 2: 1993
• 97 Ishiyama T, Matsuda N, Miyaura N, Suzuki A. J. Am. Chem. Soc. 1993; 115: 11018
• 98 Yoshida H, Kawashima S, Takemoto Y, Okada K, Ohshita J, Takaki K. Angew. Chem. Int. Ed. 2012; 51: 235
• 99 Grirrane A, Corma A, Garcia H. Chem. Eur. J. 2011; 17: 2467
• 100 Chen Q, Zhao J, Ishikawa Y, Asao N, Yamamoto Y, Jin T. Org. Lett. 2013; 15: 5766
• 101a Asao N, Nogami T, Lee S, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 10921
• 101b Sato K, Asao N, Yamamoto Y. J. Org. Chem. 2005; 70: 8977
• 101c Asao N, Sato K, Menggenbateer; Yamamoto Y. J. Org. Chem. 2005; 70: 3682
• 102a Asao N, Takahashi K, Lee S, Kasahara T, Yamamoto Y. J. Am. Chem. Soc. 2002; 124: 12650
• 102b Asao N, Aikawa H, Yamamoto Y. J. Am. Chem. Soc. 2004; 126: 7458
• 103 Abad A, Corma A, Garcia H. Top. Catal. 2007; 44: 237
• 104 Asao N, Menggenbateer; Seya Y, Yamamoto Y, Chen M, Zhang W, Inoue A. Synlett 2012; 23: 66
• 105 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 106 Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
• 107 Jin T, Yan M, Yamamoto Y. ChemCatChem 2012; 4: 1217
• 108 Cook TL, Walker JA, Mack J. Green Chem. 2013; 15: 617
• 109 Kim JY, Park JC, Kang H, Song H, Park KH. Chem. Commun. 2010; 46: 439
• 110 Alonso F, Moglie Y, Radivoy G, Yus M. Tetrahedron Lett. 2009; 50: 2358
• 111 Lipshutz BH, Taft BR. Angew. Chem. Int. Ed. 2006; 45: 8235
• 112 Yamada YM. A, Sarkar SM, Uozumi Y. J. Am. Chem. Soc. 2012; 134: 9285
• 113 Chassaing S, Kumarraja M, Souna Sido AS, Pale P, Sommer J. Org. Lett. 2007; 9: 883
• 114 Jin T, Yan M, Menggenbateer; Minato T, Bao M, Yamamoto Y. Adv. Synth. Catal. 2011; 353: 3095
• 115 Liu Z, Dong N, Xu M, Sun Z, Tu T. J. Org. Chem. 2013; 78: 7436
• 116 Wu W.-Y, Lin T.-C, Takahashi T, Tsai F.-U, Mou C.-Y. ChemCatChem 2013; 5: 1011
• 117 Lipshutz BH, Blomgren PA. J. Am. Chem. Soc. 1999; 121: 5819
• 118 Liu J, Deng Y, Wang H, Zhang H, Yu G, Wu B, Zhang H, Li Q, Marder TB, Yang Z, Lei A. Org. Lett. 2008; 10: 2661
• 119 Zhang Z, Wang Z. J. Org. Chem. 2006; 71: 7485
• 120 Gao Z, Feng Y, Cui F, Hua Z, Zhou J, Zhu Y, Shi J. J. Mol. Catal. A: Chem. 2011; 336: 51
• 121 Zhu M, Diao G. J. Phys. Chem. C 2011; 115: 24743
• 122 Niembro S, Shafir A, Vallribera A, Alibés R. Org. Lett. 2008; 10: 3215
• 123 Zeng M, Qi C, Yang J, Wang B, Zhang X.-M. Ind. Eng. Chem. Res. 2014; 53: 10041
• 124 Chen X, Hou Y, Wang H, Cao Y, He J. J. Phys. Chem. C 2008; 112: 8172
• 125 Ogasawara S, Kato S. J. Am. Chem. Soc. 2010; 132: 4608
• 126 Chen Z, Cui Z.-M, Li P, Cao C.-Y, Hong Y.-L, Wu Z, Song W.-G. J. Phys. Chem. C 2012; 116: 14986
• 127 Tanaka S, Kaneko T, Asao N, Yamamoto Y, Chen M, Zhang W, Inoue A. Chem. Commun. 2011; 47: 5985
• 128 Kaneko T, Tanaka S, Asao N, Yamamoto Y, Chen M, Inoue A. Adv. Synth. Catal. 2011; 353: 2927
• 129 Yamamoto Y. Tetrahedron 2014; 70: 2305