3.1.11 Organometallic Complexes of Zinc (Update 2014)

Abstract

Zinc salts are abundant, inexpensive, nontoxic, and exhibit environmentally benign properties. As a result, organic chemists have been interested in using zinc salts as catalysts in organic synthesis during the last three decades. In this chapter, the main contributions on zinc-catalyzed organic synthesis are summarized and discussed. Many name reactions with zinc as catalyst are included, as well as zinc-catalyzed reduction and oxidation reactions.

Key words

zinc catalysts - organic synthesis - asymmetric synthesis - C—C bond formation - C—N bond formation - C—O bond formation - reduction - oxidation

• 1 Hambidge KM, Krebs NF. J. Nutr. 2007; 137: 1101

• 2 Prasad AS. Br. Med. J. 2003; 326: 409

• 3 Maret W, Sandstead HH. J. Trace Elem. Med. Biol. 2006; 20: 3

• 4 Prasad AS, Beck FW, Grabowski SM, Kaplan J, Mathog RH. Proc. Assoc. Am. Physicians 1997; 109: 68

• 5 Rink L, Gabriel R. Proc. Nutr. Soc. 2000; 59: 541

• 6 Broadley MR, White PJ, Hammond JP, Zelko I, Lux A. New Phytol. 2007; 173: 677

• 7 Organozinc Reagents: A Practical Approach. Knochel P, Jones P. Oxford University Press; Oxford 1999

• 8 Synthetic Methods of Organometallic and Inorganic Chemistry. Herrmann WA. Thieme; Stuttgart 2002: 10

• 9 Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893

• 10 Mehta VP, Van der Eycken EV. Chem. Soc. Rev. 2011; 40: 4925

• 11 Wu X.-F, Neumann H, Beller M. Chem. Soc. Rev. 2011; 40: 4986

• 12 Chinchilla R, Nájera C. Chem. Soc. Rev. 2011; 40: 5084

• 13 McCartney D, Guiry PJ. Chem. Soc. Rev. 2011; 40: 5122

• 14 Wei H.-X, Jasoni RL, Shao H, Hu J, Pare PW. Tetrahedron 2004; 60: 11 829

• 15 Northtrup AB, MacMillan DWC. J. Am. Chem. Soc. 2002; 124: 6798

• 16 Maya V, Raj M, Singh VK. Org. Lett. 2007; 9: 2593

• 17 Jin W, Li X, Wan B. J. Org. Chem. 2011; 76: 484

• 18 Arai T, Watanabe M, Yanagisawa A. Org. Lett. 2007; 9: 3595

• 19 Xu L.-W, Xia C.-G, Li L. J. Org. Chem. 2004; 69: 8482

• 20 Kobayashi S, Kiyohara H, Yamaguchi M. J. Am. Chem. Soc. 2011; 133: 708

• 21 Reddy KR, Kumar NS. Synlett 2006; 2246

• 22 Modern Aldol Reactions. Mahrwald R. Wiley-VCH; Weinheim, Germany 2004

• 23 Irie K, Watanabe K.-i. Bull. Chem. Soc. Jpn. 1980; 53: 1366

• 24 Watanabe K.-i, Yamada Y, Goto K. Bull. Chem. Soc. Jpn. 1985; 58: 1401

• 25 Nakagawa M, Nakao H, Watanabe K.-i. Chem. Lett. 1985; 391

• 26 Nakagawa M, Maruki M, Watanabe K.-i. Chem. Lett. 1985; 1025

• 27 Trost BM, Ito H. J. Am. Chem. Soc. 2000; 122: 12 003

• 28 Trost BM, Ito H, Silcoff ER. J. Am. Chem. Soc. 2001; 123: 3367

• 29 Trost BM, Silcoff ER, Ito H. Org. Lett. 2001; 3: 2497

• 30 Trost BM, Fettes A, Shireman BT. J. Am. Chem. Soc. 2004; 126: 2660

• 31 Trost BM, Shin S, Sciafani JA. J. Am. Chem. Soc. 2005; 127: 8602

• 32 Trost BM, Yeh VSC. Org. Lett. 2002; 4: 3513

• 33 Yoshikawa N, Kumagai N, Matsunaga S, Moll G, Ohshima T, Suzuki T, Shibasaki M. J. Am. Chem. Soc. 2001; 123: 2466

• 34 Kumagai N, Matsunaga S, Yoshikawa N, Ohshima T, Shibasaki M. Org. Lett. 2001; 3: 1539

• 35 Kumagai N, Matsunaga S, Kinoshita T, Harada S, Okada S, Sakamoto S, Yamaguchi K, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 2169

• 36 Li H, Da C.-S, Xiao Y.-H, Li X, Su Y.-N. J. Org. Chem. 2008; 73: 7398

• 37 Darbre T, Dubs C, Rusanov E, Stoeckli-Evans H. Eur. J. Inorg. Chem. 2002; 3284

• 38 Simon M.-O, Li C.-J. Chem. Soc. Rev. 2012; 41: 1415

• 39 Darbre T, Machuqueiro M. Chem. Commun. (Cambridge) 2003; 1090

• 40 Kofoed J, Machuqueiro M, Reymond J.-L, Darbre T. Chem. Commun. (Cambridge) 2004; 1540

• 41 Fernandez-Lopez R, Kofoed J, Machuqueiro M, Darbre T. Eur. J. Org. Chem. 2005; 5268

• 42 Kofoed J, Reymond J.-L, Darbre T. Org. Biomol. Chem. 2005; 3: 1850

• 43 Kofoed J, Darbre T, Reymond J.-L. Chem. Commun. (Cambridge) 2006; 1482

• 44 Penhoat M, Barbry D, Rolando C. Tetrahedron Lett. 2011; 52: 159

• 45 Paradowska J, Stodulski M, Mlynarski J. Adv. Synth. Catal. 2007; 349: 1041

• 46 Paradowska J, Pasternak M, Gut B, Gryzło B, Mlynarski J. J. Org. Chem. 2012; 77: 173

• 47 Lu Z, Mei H, Zhang G, Han J, Pan Y. Sci. China Chem. 2010; 53: 2291

• 48 Chen G, Fu X, Li C, Wu C, Miao Q. J. Organomet. Chem. 2012; 702: 19

• 49 Itoh S, Kitamura M, Yamada Y, Aoki S. Chem.–Eur. J. 2009; 15: 10 570

• 50 Andreu C, Asensio G. Tetrahedron 2011; 67: 7050

• 51 Calter MA, Orr RK. Tetrahedron Lett. 2003; 44: 5699

• 52 Zhou L, Doyle MP. Org. Lett. 2010; 12: 796

• 53 Sakai S, Kikuch K, Yamauchi T, Higashiyama K. Synlett 2011; 1431

• 54 Mlynarski J, Jankowska J. Adv. Synth. Catal. 2005; 347: 521

• 55 Jankowska J, Mlynarski J. J. Org. Chem. 2006; 71: 1317

• 56 Jankowska J, Paradowska J, Rakiel B, Mlynarski J. J. Org. Chem. 2007; 72: 2228

• 57 Pasternak M, Paradowska J, Rogozinska M, Mlynarski J. Tetrahedron Lett. 2010; 51: 4088

• 58 Lai S, Zercher CK, Jasinski JP, Reid SN, Staples RJ. Org. Lett. 2001; 3: 4169

• 59 Henry L. C. R. Hebd. Seances Acad. Sci. 1895; 120: 1265

• 60 Henry L. Bull. Soc. Chim. Fr. 1895; 13: 999

• 61 Trost BM, Yeh VSC. Angew. Chem. Int. Ed. 2002; 41: 861

• 62 Trost BM, Yeh VSC, Ito H, Bremeyer N. Org. Lett. 2002; 4: 2621

• 63 Zhong Y.-W, Tian P, Lin G.-Q. Tetrahedron: Asymmetry 2004; 15: 771

• 64 Liu S, Wolf C. Org. Lett. 2008; 10: 1831

• 65 Bulut A, Aslan A, Dogan Ö. J. Org. Chem. 2008; 73: 7373

• 66 Palomo C, Oiarbide M, Laso A. Angew. Chem. Int. Ed. 2005; 44: 3881

• 67 Klein G, Pandiaraju S, Reiser O. Tetrahedron Lett. 2002; 43: 7503

• 68 Nguyen QT, Jeong JH. Polyhedron 2008; 27: 3227

• 69 Kopylovich MN, Mac Leod TCO, Mahmudov KT, Guedes da Silva MFC, Pombeiro AJL. Dalton Trans. 2011; 40: 5352

• 70 Reddy KR, Rajasekhar CV, Kirshna GG. Synth. Commun. 2007; 37: 1971

• 71 Qi N, Liao R.-Z, Yu J.-G, Liu R.-Z. J. Comput. Chem. 2010; 31: 1376

• 72 Trost BM, Lupton DW. Org. Lett. 2007; 9: 2023

• 73 Palomo C, Oiarbide M, Halder R, Laso A, López R. Angew. Chem. Int. Ed. 2006; 45: 117

• 74 Ishimaru K, Kojima T. J. Org. Chem. 2000; 65: 8395

• 75 Ishimaru K, Kojima T. Tetrahedron Lett. 2001; 42: 5037

• 76 Ishimaru K, Kojima T. J. Org. Chem. 2003; 68: 4959

• 77 Ishimaru K, Kojima T. Tetrahedron Lett. 2003; 44: 5441

• 78 Yuan Z, Wei Y, Shi M. Chin. J. Chem. 2010; 28: 1709

• 79 Yuan Z, Mei L, Wei Y, Shi M, Kattamuri PV, McDowell P, Li G. Org. Biomol. Chem. 2012; 10: 2509

• 80 Ranu BC, Samanta S, Guchhait SK. Tetrahedron 2002; 58: 983

• 81 Wu M, Jing H, Chang T. Catal. Commun. 2007; 8: 2217

• 82 Matsunaga S, Kumagai N, Harada S, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 4712

• 83 Matsunaga S, Yoshida T, Morimoto H, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2004; 126: 8777

• 84 Yoshida T, Morimoto H, Kumagai N, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2005; 44: 3470

• 85 Yamaguchi A, Matsunaga S, Shibasaki M. Tetrahedron Lett. 2006; 47: 3985

• 86 Trost BM, Jaratjaroonphong J, Reutrakui V. J. Am. Chem. Soc. 2006; 128: 2778

• 87 Kumagai N, Matsunaga S, Shibasaki M. Org. Lett. 2001; 3: 4251

• 88 Harada S, Kumagai N, Kinoshita T, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2003; 125: 2582

• 89 Trost BM, Hitce J. J. Am. Chem. Soc. 2009; 131: 4572

• 90 Lu S.-F, Du D.-M, Xu J, Zhang S.-W. J. Am. Chem. Soc. 2006; 128: 7418

• 91 Ray SK, Singh PK, Singh VK. Org. Lett. 2011; 13: 5812

• 92 Rajalakshmi V, Vijayaraghavan VR, Varghese B, Raghavan A. Inorg. Chem. 2008; 47: 5821

• 93 Guan X.-Y, Yang L.-P, Hu W. Angew. Chem. Int. Ed. 2010; 49: 2190

• 94 Ji X, Tong H, Yuan Y. Synth. Commun. 2011; 41: 372

• 95 Attanasi OA, Favi G, Filippone P, Lillini S, Mantellini F, Spinelli D, Stenta M. Adv. Synth. Catal. 2007; 349: 907

• 96 Balalaie S, Chadegani F, Darviche F, Bijanzadeh HR. Chin. J. Chem. 2009; 27: 1953

• 97 Lu S.-F, Du D.-M, Xu J. Org. Lett. 2006; 8: 2115

• 98 Liu H, Xu J, Du D.-M. Org. Lett. 2007; 9: 4725

• 99 Liu H, Lu S.-F, Xu J, Du D.-M. Chem.–Asian J. 2008; 3: 1111

• 100 Trost BM, Müller C. J. Am. Chem. Soc. 2008; 130: 2438

• 101 Niu L.-F, Xin Y.-C, Wang R.-L, Jiang F, Xu P.-F, Hui X.-P. Synlett 2010; 765

• 102 Wang B.-L, Li N.-K, Zhang J.-X, Liu G.-G, Liu T, Shen Q, Wang X.-W. Org. Biomol. Chem. 2011; 9: 2614

• 103 Yuan Z.-L, Lei Z.-Y, Shi M. Tetrahedron: Asymmetry 2008; 19: 1339

• 104 Singh PK, Singh VK. Org. Lett. 2010; 12: 80

• 105 Huang Y, Suzuki S, Liu G, Tokunaga E, Shiro M, Shibata N. New J. Chem. 2011; 35: 2614

• 106 Jia Y.-X, Zhu S.-F, Yang Y, Zhou Q.-L. J. Org. Chem. 2006; 71: 75

• 107 Salter MM, Kobayashi J, Shimizu Y, Kobayashi S. Org. Lett. 2006; 8: 3533

• 108 Hui Y, Chen W, Wang W, Jiang J, Cai Y, Lin L, Liu X, Feng X. Adv. Synth. Catal. 2010; 352: 3174

• 109 Meshram HM, Kumar DA, Reddy BC. Helv. Chim. Acta 2009; 92: 1002

• 110 Wan N, Hui Y, Xie Z, Wang J. Chin. J. Chem. 2012; 30: 311

• 111 He F, Wu H, Chen J, Su W. Synth. Commun. 2008; 38: 255

• 112 Frantz DE, Fässler R, Carreira EM. J. Am. Chem. Soc. 1999; 121: 11 245

• 113 Fässler R, Frantz DE, Oetiker J, Carreira EM. Angew. Chem. Int. Ed. 2002; 41: 3054

• 114 Frantz DE, Fässler R, Carreira EM. J. Am. Chem. Soc. 2000; 122: 1806

• 115 Anand NK, Carreira EM. J. Am. Chem. Soc. 2001; 123: 9687

• 116 Reber S, Knöpfel TF, Carreira EM. Tetrahedron 2003; 59: 6813

• 117 Fässler R, Tomooka CS, Frantz DE, Carreira EM. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5843

• 118 Jiang B, Chen Z, Tang X. Org. Lett. 2002; 4: 3451

• 119 Jiang B, Chen Z, Xiong W. Chem. Commun. (Cambridge) 2002; 1524

• 120 Chen Z, Xiong W, Jiang B. Chem. Commun. (Cambridge) 2002; 2098

• 121 Pinet S, Pandya SU, Chavant PY, Ayling A, Vallée Y. Org. Lett. 2002; 4: 1463

• 122 Patel SK, Py S, Pandya SU, Chavant PY, Vallée Y. Tetrahedron: Asymmetry 2003; 14: 525

• 123 Downey CW, Mahoney BD, Lipari VR. J. Org. Chem. 2009; 74: 2904

• 124 Hosseini-Sarvari M, Mardaneh Z. Bull. Korean Chem. Soc. 2011; 32: 4297

• 125 Ramu E, Varala R, Streelatha N, Adapa SR. Tetrahedron Lett. 2007; 48: 7184

• 126 Wang BM, Song ZL, Fan CA, Tu YQ, Shi Y. Org. Lett. 2002; 4: 363

• 127 Song ZL, Wang BM, Tu YQ, Fan CA, Zhang SY. Org. Lett. 2003; 5: 2319

• 128 Kuang J, Ma S. J. Am. Chem. Soc. 2010; 132: 1786

• 129 Ye J, Li S, Chen B, Fan W, Kuang J, Liu J, Liu Y, Miao B, Mao B, Wang Y, Xie X, Yu Q, Yuan W, Ma S. Org. Lett. 2012; 14: 1346

• 130 Yasuda M, Tsuji S, Shibata I, Baba A. J. Org. Chem. 1997; 62: 8282

• 131 Yasuda M, Tsuji S, Shigeyoshi Y, Baba A. J. Am. Chem. Soc. 2002; 124: 7440

• 132 Ceylan M, Gürdere MB, Budak Y, Kazaz C, Seçen H. Synthesis 2004; 1750

• 133 Nevar NM, Kel’in AV, Kulinkovich OG. Synthesis 2000; 1259

• 134 Chataigner I, Hess E, Toupet L, Piettre SR. Org. Lett. 2001; 3: 515

• 135 Chretien A, Chataigner I, L’Helias N, Piettre SR. J. Org. Chem. 2003; 68: 7990

• 136 Chretien A, Chataigner I, Piettre SR. Tetrahedron 2005; 61: 7907

• 137 Chopin N, Gérard H, Chataigner I, Piettre SR. J. Org. Chem. 2009; 74: 1237

• 138 Grover HK, Lebold TP, Kerr MA. Org. Lett. 2011; 13: 220

• 139 Fang X.-L, Tang R.-Y, Zhang X.-G, Zhong P, Deng C.-L, Li J.-H. J. Organomet. Chem. 2011; 696: 352

• 140 Hess W, Burton JW. Adv. Synth. Catal. 2011; 353: 2966

• 141 Liu C.-R, Li M.-B, Yang C.-F, Tian S.-K. Chem.–Eur. J. 2009; 15: 793

• 142 Studte C, Breit B. Angew. Chem. Int. Ed. 2008; 47: 5451

• 143 Brand GJ, Studte C, Breit B. Org. Lett. 2009; 11: 4668

• 144 Hatano M, Suzuki S, Ishihara K. J. Am. Chem. Soc. 2006; 128: 9998

• 145 Hatano M, Suzuki S, Ishihara K. Synlett 2010; 321

• 146 Hatano M, Ito O, Suzuki S, Ishihara K. J. Org. Chem. 2010; 75: 5008

• 147 Hatano M, Ito O, Suzuki S, Ishihara K. Chem. Commun. (Cambridge) 2010; 46: 2674

• 148 Armstrong DR, Clegg W, García-Alvarez P, McCall MD, Nuttall L, Kennedy AR, Russo L, Hevia E. Chem.–Eur. J. 2011; 17: 4470

• 149 Armstrong DR, Clegg W, García-Alvarez P, Kennedy AR, McCall MD, Russo L, Hevia E. Chem.–Eur. J. 2011; 17: 8333

• 150 Kiyokawa K, Tachikake N, Yasuda M, Baba A. Angew. Chem. Int. Ed. 2011; 50: 10 393

• 151 Andreev AA, Konshin VV, Komarov NV, Rubin M, Brouwer C, Gevorgyan V. Org. Lett. 2004; 6: 421

• 152 Rahaim Jr RJ, Shaw JT. J. Org. Chem. 2008; 73: 2912

• 153 Nakamura S, Uchiyama M, Ohwada T. J. Am. Chem. Soc. 2004; 126: 11 146

• 154 Murakami K, Yorimitsu H, Oshima K. J. Org. Chem. 2009; 74: 1415

• 155 Liu G.-B. Synlett 2006; 1431

• 156 Mukherjee D, Thompson RR, Ellern A, Sadow AD. ACS Catal. 2011; 1: 698

• 157 Yang Y.-Y, Shou W.-G, Wang Y.-G. Tetrahedron 2006; 62: 10 079

• 158 Kassaee MZ, Movahedi F, Masrouri H. Synlett 2009; 1326

• 159 Disale ST, Kale SR, Kahandal SS, Srinivasan TG, Jayaram RV. Tetrahedron Lett. 2012; 53: 2277

• 160 Bernard L, Zhuang W, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 5772

• 161 Pachon LD, Gamez P, van Brussel JJM, Reedijk J. Tetrahedron Lett. 2003; 44: 6025

• 162 Bonollo S, Fringuelli F, Pizzo F, Vaccaro L. Synlett 2008; 1574

• 163 Amantini D, Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L. Synlett 2003; 2292

• 164 Fringuelli F, Pizzo F, Tortoioli S, Vaccaro L. J. Org. Chem. 2003; 68: 8248

• 165 Tamaddon F, Aboee F, Nasiri A. Catal. Commun. 2011; 16: 194

• 166 Shekhar AC, Kumar AR, Sathaiah G, Paul VL, Sridhar M, Rao PS. Tetrahedron Lett. 2009; 50: 7099

• 167 Tamaddon F, Sabeti MR, Jafari AA, Tirgir F. J. Mol. Catal. A: Chem. 2011; 351: 41

• 168 Sharghi H, Hosseini M. Synthesis 2002; 1057

• 169 Alex K, Tillack A, Schwarz N, Beller M. ChemSusChem 2008; 1: 333

• 170 Tsuchimoto T, Aoki K, Wagatsuma T, Suzuki Y. Eur. J. Org. Chem. 2008; 4035

• 171 Zulys A, Dochnahl M, Hollmann D, Löhnwitz K, Herrmann J.-S, Roesky PW, Blechert S. Angew. Chem. Int. Ed. 2005; 44: 7794

• 172 Jenter J, Lühl A, Roesky PW, Blechert S. J. Organomet. Chem. 2011; 696: 406

• 173 Dochnahl M, Pissarek J.-W, Blechert S, Löhnwitz K, Roesky PW. Chem. Commun. (Cambridge) 2006; 3405

• 174 Dochnahl M, Löhnwitz K, Pissarek J.-W, Biyikal M, Schulz SR, Schön S, Meyer N, Roesky PW, Blechert S. Chem.–Eur. J. 2007; 13: 6654

• 175 Dochnahl M, Löhnwitz K, Pissarek J.-W, Roesky PW, Blechert S. Dalton Trans. 2008; 2844

• 176 Duncan C, Biradar AV, Asefa T. ACS Catal. 2011; 1: 736

• 177 Hirrillo-Martínez P, Hultzsch KC. Tetrahedron Lett. 2009; 50: 2054

• 178 Pissarek J.-W, Schlesiger D, Roesky PW, Blechert S. Adv. Synth. Catal. 2009; 351: 2081

• 179 Liu G.-Q, Li Y.-M. Tetrahedron Lett. 2011; 52: 7168

• 180 Liu G.-Q, Li W, Wang Y.-M, Ding Z.-Y, Li Y.-M. Tetrahedron Lett. 2012; 53: 4393

• 181 Tseng M.-C, Chu Y.-H. Tetrahedron 2008; 64: 9515

• 182 Heravi MM, Tegrani MH, Bakhtiari K, Oskooie HA. Catal. Commun. 2007; 8: 1341

• 183 Jacob RG, Dutra LG, Radatz CS, Mendes SR, Perin G, Lenardão EJ. Tetrahedron Lett. 2009; 50: 1495

• 184 Sivamurugan V, Kumar RS, Palanichamy M, Murugesan V. J. Heterocycl. Chem. 2005; 42: 969

• 185 Sivamurugan V, Deepa K, Palanichamy M, Murugesan V. Synth. Commun. 2004; 34: 3833

• 186 Bahrami K, Khodaei MM, Farrokhi A. Synth. Commun. 2009; 39: 1801

• 187 Sridhar M, Ramanaiah BC, Narsaiah C, Mahesh B, Kumaraswamy M, Mallu KKR, Ankathi VM, Rao PS. Tetrahedron Lett. 2009; 50: 3897

• 188 Sasada T, Kobayashi F, Sakai N, Konakahara T. Org. Lett. 2009; 11: 2161

• 189 Liu X.-t, Hao L, Chen L, Zhan Z.-p. Org. Biomol. Chem. 2010; 8: 3064

• 190 Attanasi OA, Berretta S, De Crescentini L, Favi G, Giorgi G, Mantellini F, Nicolini S. Adv. Synth. Catal. 2011; 353: 595

• 191 Ranu BC, Ghosh S, Das A. Mendeleev Commun. 2006; 16: 220

• 192 Dong H, Shen M, Redford JE, Stokes BJ, Pumphrey AL, Driver TG. Org. Lett. 2007; 9: 5191

• 193 Wyrębek P, Sniady A, Bewick N, Li Y, Mikus A, Wheeler KA, Dembinski R. Tetrahedron 2009; 65: 1268

• 194 Karapetyan V, Mkrtchyan S, Schmidt A, Attanasi OA, Favi G, Mantellini F, Villinger A, Fischer C, Langer P. Adv. Synth. Catal. 2008; 350: 1331

• 195 He S, Chen L, Niu Y.-N, Wu L.-Y, Liang Y.-M. Tetrahedron Lett. 2009; 50: 2443

• 196 Kidwai M, Jain A, Poddar R. J. Organomet. Chem. 2011; 696: 1939

• 197 Alex K, Tillack A, Schwarz N, Beller M. Org. Lett. 2008; 10: 2377

• 198 Dogan Ö, Koyuncu H, Garner P, Bulut A, Youngs WJ, Panzner M. Org. Lett. 2006; 8: 4687

• 199 Lebold TP, Leduc AB, Kerr MA. Org. Lett. 2009; 11: 3770

• 200 Yamazaki S, Morikawa S, Miyazaki K, Takebayashi M, Yamamoto Y, Morimoto T, Kakiuchi K, Mikata Y. Org. Lett. 2009; 11: 2796

• 201 Yin Y, Ma W, Chai Z, Zhao G. J. Org. Chem. 2007; 72: 5731

• 202 Cao H, Diaz DI, DiCesare N, Lakowicz JR, Heagy MD. Org. Lett. 2002; 4: 1503

• 203 Wang L.-M, Hu L, Shao J.-H, Yu J, Zhang L. J. Fluorine Chem. 2008; 129: 1139

• 204 Li Y, Zou H, Gong J, Xiang J, Luo T, Quan J, Wang G, Yang Z. Org. Lett. 2007; 9: 4057

• 205 Ohshima T, Iwasaki T, Mashima K. Chem. Commun. (Cambridge) 2006; 2711

• 206 Xia Q, Ganem B. Org. Lett. 2002; 4: 1631

• 207 Kumar MP, Liu R.-S. J. Org. Chem. 2006; 71: 4951

• 208 Makarycheva-Mikhailova AV, Kukushkin VYu, Nazarov AA, Garnovskii DA, Pombeiro AJL, Haukka M, Keppler BN, Galanski M. Inorg. Chem. 2003; 42: 2805

• 209 Tamaddon F, Amrollahi MA, Sharafat L. Tetrahedron Lett. 2005; 46: 7841

• 210 Sarvari MH, Sharghi H. Tetrahedron 2005; 61: 10 903

• 211 Trost BM, Malhotra S, Mino T, Rajapaksa NS. Chem.–Eur. J. 2008; 14: 7648

• 212 Solhy A, Clark JH, Tahir R, Sebti S, Larzek M. Green Chem. 2006; 8: 871

• 213 Mino T, Hasegawa T, Shirae Y, Sakamoto M, Fujita T. J. Organomet. Chem. 2007; 692: 4389

• 214 Pericas A, Shafir A, Vallribera A. Tetrahedron 2008; 64: 9258

• 215 Iwasaki T, Maegawa Y, Hayashi Y, Ohshima T, Mashima K. Synlett 2009; 1659

• 216 Chavan SP, Shivasankar K, Sivappa R, Kale R. Tetrahedron Lett. 2002; 43: 8583

• 217 Ranu BC, Dutta J, Das A. Chem. Lett. 2003; 32: 366

• 218 Kumar R, Thilagavathi R, Gulhane R, Chakraborti AK. J. Mol. Catal. A: Chem. 2006; 250: 226

• 219 Du H, Long J, Hu J, Li X, Ding K. Org. Lett. 2002; 4: 4349

• 220 Du H, Ding K. Org. Lett. 2003; 5: 1091

• 221 Du H, Zhang X, Wang Z, Ding K. Tetrahedron 2005; 61: 9465

• 222 Sniady A, Durham A, Morreale MS, Wheeler KA, Dembinski R. Org. Lett. 2007; 9: 1175

• 223 Sniady A, Durham A, Morreale MS, Marcinek A, Szafert S, Lis T, Brzezinska KR, Iwasaki T, Ohshima T, Mashima K, Dembinski R. J. Org. Chem. 2008; 73: 5881

• 224 Méndez-Andino J, Paquette LA. Org. Lett. 2000; 2: 4095

• 225 Wang A, Jiang H, Xu Q. Synlett 2009; 929

• 226 Aschwanden P, Frantz DE, Carreira EM. Org. Lett. 2000; 2: 2331

• 227 Nakamura M, Liang C, Nakamura E. Org. Lett. 2004; 6: 2015

• 228 Mahajan VA, Shinde PD, Gajare AS, Karthikeyan M, Wakharkar RD. Green Chem. 2002; 4: 325

• 229 Kim HS, Kim JJ, Lee BG, Jung OS, Jang HG, Kang SO. Angew. Chem. Int. Ed. 2000; 39: 4096

• 230 Moore DR, Cheng M, Lobkovsky EB, Coates GW. J. Am. Chem. Soc. 2003; 125: 11 911

• 231 Nakano K, Nozaki K, Hiyama T. J. Am. Chem. Soc. 2003; 125: 5501

• 232 Ohkuma T, Hashiguchi S, Noyori R. J. Org. Chem. 1994; 59: 217

• 233 Bell NA, Kassyk AL. Inorg. Chim. Acta 1996; 250: 345

• 234 Ranu BC. Synlett 1993; 885

• 235 Mimoun H. J. Org. Chem. 1999; 64: 2582

• 236 Bette V, Mortreux A, Lehmann CW, Carpentier J.-F. Chem. Commun. (Cambridge) 2003; 332

• 237 Bette V, Mortreux A, Savoia D, Carpentier J.-F. Adv. Synth. Catal. 2005; 347: 289

• 238 Marinos NA, Enthaler S, Driess M. ChemCatChem 2010; 2: 846

• 239 Enthaler S, Eckhardt B, Inoue S, Irran E, Driess M. Chem.–Asian J. 2010; 5: 2027

• 240 Enthaler S, Schröder K, Inoue S, Eckhardt B, Junge K, Beller M, Driess M. Eur. J. Org. Chem. 2010; 4893

• 241 Chen L.-Z, Peng J.-J, Li J.-Y, Bai Y, Hu Y.-Q, Qiu H.-Y, Wu H, Lai G.-Q. Lett. Org. Chem. 2008; 5: 591

• 242 Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. J. Am. Chem. Soc. 1999; 121: 6158

• 243 Roh SG, Yoon JU, Jeong JH. Polyhedron 2004; 23: 2063

• 244 Bette V, Mortreux A, Savoia D, Carpentier J.-F. Tetrahedron 2004; 60: 2837

• 245 Bette V, Mortreux A, Ferioli F, Martelli G, Savoia D, Carpentier J.-F. Eur. J. Org. Chem. 2004; 3040

• 246 Mastranzo VM, Quintero L, de Parrodi CA, Juaristi E, Walsh PJ. Tetrahedron 2004; 60: 1781

• 247 Ushio H, Mikami K. Tetrahedron Lett. 2005; 46: 2903

• 248 Bandini M, Melucci M, Piccinelli F, Sinisi R, Tommasi S, Umani-Ronchi A. Chem. Commun. (Cambridge) 2007; 4519

• 249 Inagaki T, Yamada Y, Phong LT, Furuta A, Ito J.-i, Nishiyama H. Synlett 2009; 253

• 250 Santacruz E, Huelgas G, Angulo SK, Mastranzo VM, Hernández-Ortega S, Aviña JA, Juaristi E, de Parrodi CA, Walsh PJ. Tetrahedron: Asymmetry 2009; 20: 2788

• 251 Gajewy J, Kwit M, Gawroński J. Adv. Synth. Catal. 2009; 351: 1055

• 252 Bandini M, Cozzi PG, Angelis M, Umani-Ronchi A. Tetrahedron Lett. 2000; 41: 1601

• 253 Locatelli M, Cozzi PG. Angew. Chem. Int. Ed. 2003; 42: 4928

• 254 Gérard S, Pressel Y, Riant O. Tetrahedron: Asymmetry 2005; 16: 1889

• 255 Junge K, Möller K, Wendt B, Das S, Gördes D, Thurow K, Beller M. Chem.–Asian J. 2012; 7: 314

• 256 Liu S, Peng J, Yang H, Bai Y, Li J, Lai G. Tetrahedron 2012; 68: 1371

• 257 Panosyan FB, Chin J. Org. Lett. 2003; 5: 3947

• 258 Ireland T, Fontanet F, Tchao G.-G. Tetrahedron Lett. 2004; 45: 4383

• 259 Park B.-M, Mun S, Yun J. Adv. Synth. Catal. 2006; 348: 1029

• 260 Park B.-M, Feng X, Yun J. Bull. Korean Chem. Soc. 2011; 32: 2960

• 261 Gajewy J, Gawronski J, Kwit M. Org. Biomol. Chem. 2011; 9: 3863

• 262 Enthaler S. Catal. Lett. 2011; 141: 55

• 263 Werkmeister S, Fleischer S, Zhou S, Junge K, Beller M. ChemSusChem 2012; 5: 777

• 264 Shono T, Kise N, Nomura R, Yamanami A. Tetrahedron Lett. 1993; 34: 3577

• 265 Pansare SV, Malusare MG. Tetrahedron Lett. 1996; 37: 2859

• 266 Kise N, Ueda N. Tetrahedron Lett. 2001; 42: 2365

• 267 Das S, Möller K, Junge K, Beller M. Chem.–Eur. J. 2011; 17: 7414

• 268 Das S, Addis D, Zhou S, Junge K, Beller M. J. Am. Chem. Soc. 2010; 132: 1770

• 269 Das S, Zhou S, Addis D, Enthaler S, Junge K, Beller M. Top. Catal. 2010; 53: 979

• 270 Das S, Addis D, Junge K, Beller M. Chem.–Eur. J. 2011; 17: 12 186

• 271 Enthaler S. Catal. Sci. Technol. 2011; 1: 104

• 272 Minatti A, Dötz KH. Synlett 2004; 1634

• 273 Minatti A, Dötz KH. Eur. J. Org. Chem. 2006; 268

• 274 Wang H, Wang Z, Ding K. Tetrahedron Lett. 2009; 50: 2200

• 275 Cao HT, Grée R. Tetrahedron Lett. 2009; 50: 1493

• 276 Muthupandi P, Sekar G. Tetrahedron Lett. 2011; 52: 692

• 277 Muthupandi P, Sekar G. Tetrahedron: Asymmetry 2011; 22: 512

• 278 Kalita B, Lamar AA, Nicholas KM. Chem. Commun. (Cambridge) 2008; 4291

• 279 Wu X.-F. Tetrahedron Lett. 2012; 53: 3397

• 280 Wu X.-F. Chem.–Eur. J. 2012; 18: 8912

• 281 Wu X.-F. Tetrahedron Lett. 2012; 53: 4328

• 282 Song Z.-Z, Gong J.-L, Zhang M, Wu X.-F. Asian J. Org. Chem. 2012; 1: 214

• 283 Wu X.-F. Tetrahedron Lett. 2012; 53: 6123

• 284 Zhang M, Wu X.-F. Tetrahedron Lett. 2013; 54: 1059

• 285 Wu X.-F, Bheeter CB, Neumann H, Dixneuf PH, Beller M. Chem. Commun. (Cambridge) 2012; 48: 12 237

• 286 Enthaler S, Weidauer M, Schröder F. Tetrahedron Lett. 2012; 53: 882

• 287 Allen CL, Burel C, Williams JMJ. Tetrahedron Lett. 2010; 51: 2724

• 288 Manjula K, Pasha MA. Synth. Commun. 2007; 37: 1545

• 289 Enthaler S, Inoue S. Chem.–Asian J. 2012; 7: 169