18.4.45 Acyclic and Cyclic Carbonic Acids and Esters, and Their Sulfur, Selenium, and Tellurium Analogues (Update 2013)

R. Zimmer; D. Trawny

Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of acyclic and cyclic carbonic acid derivatives, and their sulfur, selenium, and tellurium analogues. It is mainly focused on the literature published in the period 2005–2012. Moreover, special focus is given to the application of the title compounds.

Key words

carbonates - formates - chloroformates - thiocarbonyl compounds - dithiocarbonates - selenium compounds - green chemistry - coupling reactions - carbon—oxygen bonds

• 1 Shaikh AA, Sivaram S. Chem. Rev. 1996; 96: 951

• 2 Tundo P, Selva M. Acc. Chem. Res. 2002; 35: 706

• 3 Chankeshwara SV. Synlett 2008; 624

• 4 Arico F, Tundo P. Russ. Chem. Rev. (Engl. Transl.) 2010; 79: 479

• 5 Schäffner B, Schäffner F, Verevkin SP, Börner A. Chem. Rev. 2010; 110: 4554

• 6 Keller N, Rebmann G, Keller V. J. Mol. Catal. A: Chem. 2010; 317: 1

• 7 Andraos J. Pure Appl. Chem. 2012; 84: 827

• 8 Yoshida M. Chem. Pharm. Bull. 2012; 60: 285

• 9 Mohapatra DK. Synlett 2001; 1995

• 10 Hamley P, In: Encyclopedia of Reagents for Organic Synthesis Paquette LA, Crich D, Fuchs PL, Molander GA. Wiley New York 2009; 10. 7978

• 11 Eckert H. Chim. Oggi 2011; 29: 40

• 12 Krishnaswamy D. Synlett 2000; 1860

• 13 Štambaský J, Kapras V, Štefko M, Kysilka O, Hocek M, Malkov AV, Kočovský P. J. Org. Chem. 2011; 76: 7781

• 14 Singh SJ, Jayaram RV. Tetrahedron Lett. 2008; 49: 4249

• 15 Banerjee S, Voit B, Heinrich G, Böhme F. Tetrahedron Lett. 2012; 53: 2236

• 16 Chankeshwara SV, Chebolu R, Chakraborti AK. J. Org. Chem. 2008; 73: 8615

• 17 Chebolu R, Chankeshwara SV, Chakraborti AK. Synthesis 2008; 1448

• 18 Suryakiran N, Prabhakar P, Venkateswarlu Y. Synth. Commun. 2008; 38: 177

• 19 Trost BM, Martos-Redruejo A. Org. Lett. 2009; 11: 1071

• 20 Bartoli G, Bosco M, Carlone A, Dalpozzo R, Locatelli M, Melchiorre P, Palazzi P, Sembri L. Synlett 2006; 2104

• 21 Procopio A, Cravotto G, Oliverio M, Costanzo P, Nardi M, Paonessa R. Green Chem. 2011; 13: 436

• 22 Lee S, Paek S.-M, Yun H, Kim N.-J, Suh Y.-G. Org. Lett. 2011; 13: 3344

• 23 Han YT, Kim N.-J, Jung J.-W, Yun H, Lee S, Suh Y.-G. Arch. Pharm. Res. 2011; 34: 1437

• 24 Faller JW, Sarantopoulos N. Organometallics 2004; 23: 2179

• 25 Štambaský J, Malkov AV, Kočovský P. Collect. Czech. Chem. Commun. 2008; 73: 705

• 26 Bühler S, Lagoja I, Giegrich H, Stengele K.-P, Pfleiderer W. Helv. Chim. Acta 2004; 87: 620

• 27 Literák J, Wirz J, Klán P. Photochem. Photobiol. Sci. 2005; 4: 43

• 28 Morère A, Mouffouk F, Leiris S, Leydat A, Montero J.-L. J. Carbohydr. Chem. 2006; 25: 451

• 29 Bartoli G, Bosco M, Carlone A, Locatelli M, Marcantoni E, Melchiorre P, Palazzi P, Sambri L. Eur. J. Org. Chem. 2006; 4429

• 30 Denmark SE, Regens CS, Kobayashi T. J. Am. Chem. Soc. 2007; 129: 2774

• 31 Saito Y, Yoshimura Y, Takahata H. Tetrahedron Lett. 2010; 51: 6915

• 32 Barile F, Bassetti M, D’Annibale A, Gerometta R, Palazzi M. Eur. J. Org. Chem. 2011; 6519

• 33 Carafa M, Mesto E, Quaranta E. Eur. J. Org. Chem. 2011; 2458

• 34 Jana A, Ikbal M, Singh NDP. Tetrahedron 2012; 68: 1128

• 35 Zhao S.-C, Ji K.-G, Lu L, He T, Zhou A.-X, Yan R.-L, Ali S, Liu X.-Y, Liang Y.-M. J. Org. Chem. 2012; 77: 2763

• 36 Kaiser A, Richert C. Synlett 2010; 2267

• 37 McClure MS, Berry MB, Caine D, Crawford C, Crump BC, Glover BN, Kedia SB, Millar A, Mitchell MB, Nichols CJ, Patterson DE, Powers J. Eur. J. Org. Chem. 2012; 3561

• 38 Chmielewski MK, Tykarska E, Markiewicz WT, Rypniewski W. New J. Chem. 2012; 36: 603

• 39 Hatano M, Kamiya S, Moriyama K, Ishihara K. Org. Lett. 2011; 13: 430

• 40 Hatano M, Kamiya S, Ishihara K. Chem. Commun. (Cambridge) 2012; 48: 9465

• 41 Veldurthy B, Clacens J.-M, Figueras F. Eur. J. Org. Chem. 2005; 1972

• 42 Abaee MS, Akbarzadeh E, Sharifi R, Mojtahedi MM. Monatsh. Chem. 2010; 141: 757

• 43 Selva M, Noè M, Perosa A, Gottardo M. Org. Biomol. Chem. 2012; 10: 6569

• 44 Yang Z.-Z, He L.-N, Dou X.-Y, Chanfreau S. Tetrahedron Lett. 2010; 51: 2931

• 45 Mutlu H, Ruiz J, Solleder SC, Meier MAR. Green Chem. 2012; 14: 1728

• 46 Kantam ML, Pal U, Sreedhar B, Choudary BM. Adv. Synth. Catal. 2007; 349: 1671

• 47 Adam F, Wong M.-S. Catal. Commun. 2011; 13: 87

• 48 Motokura K, Tada M, Iwasawa Y. J. Am. Chem. Soc. 2007; 129: 9540

• 49 Motokura K, Viswanadham N, Dhar GM, Iwasawa Y. Catal. Today 2009; 141: 19

• 50 Aoki S, Kotani S, Sugiura M, Nakajima M. Tetrahedron Lett. 2010; 51: 3547

• 51 Wingstrand E, Lundgren S, Penhoat M, Moberg C. Pure Appl. Chem. 2006; 78: 409

• 52 Belokon’ YuN, Clegg W, Harrington RW, Ishibashi E, Nomura H, North M. Tetrahedron 2007; 63: 9724

• 53 Belokon’ YuN, Blacker AJ, Carta P, Clutterbuck LA, North M. Tetrahedron 2004; 60: 10 433

• 54 Belokon’ YuN, Blacker AJ, Clutterbuck LA, North M. Org. Lett. 2003; 5: 4505

• 55 Khan NH, Sadhukhan A, Maity NC, Kureshy RI, Abdi SHR, Saravanan S, Bajaj HC. Tetrahedron 2011; 67: 7073

• 56 Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Prathap KJ, Jasra RV. Eur. J. Org. Chem. 2008; 4511

• 57 Lundgren S, Wingstrand E, Moberg C. Adv. Synth. Catal. 2007; 349: 364

• 58 Lundgren S, Wingstrand E, Penhoat M, Moberg C. J. Am. Chem. Soc. 2005; 127: 11 592

• 59 Gou S, Wang J, Liu X, Wang W, Chen F.-X, Feng X. Adv. Synth. Catal. 2007; 349: 343

• 60 Gou S, Chen X, Xiong Y, Feng X. J. Org. Chem. 2006; 71: 5732

• 61 Yamagiwa N, Tian J, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 3413

• 62 Tian J, Yamagiwa N, Matsunaga S, Shibasaki M. Angew. Chem. 2002; 114: 3788 Angew. Chem. Int. Ed. 2002; 41: 3636

• 63 Casas J, Baeza A, Sansano JM, Nájera C, Saá JM. Tetrahedron: Asymmetry 2003; 14: 197

• 64 Wang J, Wang W, Li W, Hu X, Shen K, Tan C, Liu X, Feng X. Chem.–Eur. J. 2009; 15: 11 642

• 65 Li Q, Chang L, Liu X, Feng X. Synlett 2006; 1675

• 66 Brunel J.-M, Holmes IP. Angew. Chem. 2004; 116: 2810 Angew. Chem. Int. Ed. 2004; 43: 2752

• 67 Trost BM, Xu J. J. Org. Chem. 2007; 72: 9372

• 68 Trost BM, Koller R, Schäffner B. Angew. Chem. 2012; 124: 8415 Angew. Chem. Int. Ed. 2012; 51: 8290

• 69 Arakawa H, Aresta M, Armor JN, Barteau MA, Beckman EJ, Bell AT, Bercaw JE, Creutz C, Dinjus E, Dixon DA, Domen K, DuBois DL, Eckert J, Fujita E, Gibson DH, Goddard WA, Goodman DW, Keller J, Kubas GJ, Kung HH, Lyons JE, Manzer LE, Marks TJ, Morokuma K, Nicholas KM, Periana R, Que L, Rostrup-Nielson J, Sachtler WMH, Schmidt LD, Sen A, Somorjai GA, Stair PC, Stults BR, Tumas W. Chem. Rev. 2001; 101: 953

• 70 Song C. Catal. Today 2006; 115: 2

• 71 Aresta M, Dibenedetto A. Dalton Trans. 2007; 2975

• 72 Sakakura T, Choi J.-C, Yasuda H. Chem. Rev. 2007; 107: 2365

• 73 Omae I. Coord. Chem. Rev. 2012; 256: 1384

• 74 Chaturvedi D, Mishra N, Mishra V. Tetrahedron Lett. 2007; 48: 5043

• 75 Gasc F, Thiebaud-Roux S, Mouloungui Z. J. Supercrit. Fluids 2009; 50: 46

• 76 Yamazaki Y, Kakuma K, Du Y, Saito S. Tetrahedron 2010; 66: 9675

• 77 Della Ca’ N, Gabriele B, Ruffolo G, Veltri L, Zanetta T, Costa M. Adv. Synth. Catal. 2011; 353: 133

• 78 Wu XL, Xiao M, Meng YZ, Lu YX. J. Mol. Catal. A: Chem. 2005; 238: 158

• 79 Wang H, Wang M, Zhang W, Zhao N, Wei W, Sun Y. Catal. Today 2006; 115: 107

• 80 Dibenedetto A, Pastore C, Aresta M. Catal. Today 2006; 115: 88

• 81 Yoshida Y, Arai Y, Kado S, Kunimori K, Tomishige K. Catal. Today 2006; 115: 95

• 82 Kohno K, Choi J.-C, Ohshima Y, Yili A, Yasuda H, Sakakura T. J. Organomet. Chem. 2008; 693: 1389

• 83 Choi J.-C, Kohno K, Ohshima Y, Yasuda H, Sakakura T. Catal. Commun. 2008; 9: 1630

• 84 Eta V, Mäki-Arvela P, Salminen E, Salmi T, Murzin DYu, Mikkola J.-P. Catal. Lett. 2011; 141: 1254

• 85 Masui Y, Haga S, Onaka M. Chem. Lett. 2011; 40: 1408

• 86 Laurenczy G, Picquet M, Plasseraud L. J. Organomet. Chem. 2011; 696: 1904

• 87 Li J, Hu J, Gu Y, Mei F, Li G. J. Mol. Catal. A: Chem. 2011; 340: 53

• 88 Li J, Hu J, Li G. Catal. Commun. 2011; 12: 1401

• 89 Parrish JP, Salvatore RN, Jung KW. Tetrahedron 2000; 56: 8207

• 90 Jorapur YR, Chi DY. J. Org. Chem. 2005; 70: 10 774

• 91 Waddell DC, Thiel I, Bunger A, Nkata D, Maloney A, Clark T, Smith B, Mack J. Green Chem. 2011; 13: 3156

• 92 Hall A, Jones KL, Jones TC, Killeen NM, Pörzig R, Taylor PH, Yau SC, Tomkinson NCO. Synlett 2006; 3435

• 93 Zhang X, Fu C, Ma S. Org. Lett. 2011; 13: 1920

• 94 Guo Y, Chen Q.-Y. J. Fluorine Chem. 2000; 102: 105

• 95 Guo Y, Shreeve JM. J. Fluorine Chem. 2007; 128: 1280

• 96 Schäffner B, Verevkin SP, Börner A. Chem. Unserer Zeit 2009; 43: 12

• 97 Banwell MG, Coster MJ, Edwards AJ, Vögtle M. Aust. J. Chem. 2003; 56: 577

• 98 Uozumi Y, Suzuka T, Kawade R, Takenaka H. Synlett 2006; 2109

• 99 Bi H.-P, Liu X.-Y, Gou F.-R, Guo L.-N, Duan X.-H, Shu X.-Z, Liang Y.-M. Angew. Chem. 2007; 119: 7198 Angew. Chem. Int. Ed. 2007; 46: 7068

• 100 Trost BM, Xu J, Reichle M. J. Am. Chem. Soc. 2007; 129: 282

• 101 Trost BM, Xu J, Schmidt T. J. Am. Chem. Soc. 2008; 130: 11 852

• 102 Lian X, Ma S. Angew. Chem. 2008; 120: 8379 Angew. Chem. Int. Ed. 2008; 47: 8255

• 103 Shu W, Jia G, Ma S. Angew. Chem. 2009; 121: 2826 Angew. Chem. Int. Ed. 2009; 48: 2788

• 104 Trost BM, Xu J, Schmidt T. J. Am. Chem. Soc. 2009; 131: 18 343

• 105 Trost BM, Lehr K, Michaelis DJ, Xu J, Buckl AK. J. Am. Chem. Soc. 2010; 132: 8915

• 106 Trost BM, Schäffner B, Osipov M, Wilton DAA. Angew. Chem. 2011; 123: 3610 Angew. Chem. Int. Ed. 2011; 50: 3548

• 107 Soheili A, Tambar UK. J. Am. Chem. Soc. 2011; 133: 12 956

• 108 Hollingworth C, Hazari A, Hopkinson MN, Tredwell M, Benedetto E, Huiban M, Gee AD, Brown JM, Gouverneur V. Angew. Chem. 2011; 123: 2661 Angew. Chem. Int. Ed. 2011; 50: 2613

• 109 Trost BM, Michaelis DJ, Charpentier J, Xu J. Angew. Chem. 2012; 124: 208 Angew. Chem. Int. Ed. 2012; 51: 204

• 110 Zhu Y, Rawal VH. J. Am. Chem. Soc. 2012; 134: 111

• 111 Gordillo A, Lloyd-Jones GC. Chem.–Eur. J. 2012; 18: 2660

• 112 Zimmer R, Reissig H.-U, In: Modern Allene Chemistry Krause N, Hashmi ASK. Wiley-VCH Weinheim, Germany 2004; 847–876

• 113 Yu C, Zhou A, He J. RSC Adv. 2012; 2: 8627

• 114 Hirashita T, Suzuki Y, Tsuji H, Sato Y, Naito K, Araki S. Eur. J. Org. Chem. 2012; 5668

• 115 Liu W.-B, Zheng C, Zhuo C.-X, Dai L.-X, You S.-L. J. Am. Chem. Soc. 2012; 134: 4812

• 116 Hassan A, Zbieg JR, Krische MJ. Angew. Chem. 2011; 123: 3555 Angew. Chem. Int. Ed. 2011; 50: 3493

• 117 Fukuoka S, Kawamura M, Komiya K, Tojo M, Hachiya H, Hasegawa K, Aminaka M, Okamoto H, Fukawa I, Konno S. Green Chem. 2003; 5: 497

• 118 Clegg W, Harrington RW, North M, Pizzato F, Villuendas P. Tetrahedron: Asymmetry 2010; 21: 1262

• 119 Ota H, Wang X, Yasukawa E. J. Electrochem. Soc. 2004; 151: A427

• 120 Sakakura T, Kohno K. Chem. Commun. (Cambridge) 2009; 1312

• 121 Sprott KT, Corey EJ. Org. Lett. 2003; 5: 2465

• 122 Nicolaou KC, Renaud J, Nantermet PG, Couladouros EA, Guy RK, Wrasidlo W. J. Am. Chem. Soc. 1995; 117: 2409

• 123 Rannard SP, Davis NJ. Org. Lett. 1999; 1: 933

• 124 Arkoudis E, Lykakis IN, Gryparis C, Stratakis M. Org. Lett. 2009; 11: 2988

• 125 Palimkar SS, Uenishi J. Org. Lett. 2010; 12: 4160

• 126 Davies SG, Fletcher AM, Kurosawa W, Lee JA, Poce G, Roberts PM, Thomson JE, Williamson DM. J. Org. Chem. 2010; 75: 7745

• 127 Cheong JY, Bae HJ, Baskar B, Thangadurai D, Kim M.-J, Rhee YH. Bull. Korean Chem. Soc. 2009; 30: 1239

• 128 Lim C, Rao MS, Shin S. Synlett 2010; 368

• 129 Kayaki Y, Yamamoto M, Ikariya T. Angew. Chem. 2009; 121: 4258 Angew. Chem. Int. Ed. 2009; 48: 4194

• 130 Yoshida S, Fukui K, Kikuchi S, Yamada T. J. Am. Chem. Soc. 2010; 132: 4072

• 131 Aoyagi N, Furusho Y, Endo T. Chem. Lett. 2012; 41: 240

• 132 Ema T, Miyazaki Y, Koyama S, Yano Y, Sakai T. Chem. Commun. (Cambridge) 2012; 48: 4489

• 133 Dou X.-Y, Wang J.-Q, Du Y, Wang E, He L.-N. Synlett 2007; 3058

• 134 Gao J, Song Q.-W, He L.-N, Liu C, Yang Z.-Z, Han X, Li X.-D, Song Q.-C. Tetrahedron 2012; 68: 3835

• 135 Sakai T, Tsutsumi Y, Ema T. Green Chem. 2008; 10: 337

• 136 Shibata I, Mitani I, Imakuni A, Baba A. Tetrahedron Lett. 2011; 52: 721

• 137 Caló V, Nacci A, Monopoli A, Fanizzi A. Org. Lett. 2002; 4: 2561

• 138 Decortes A, Martínez Belmonte M, Benet-Buchholz J, Kleij AW. Chem. Commun. (Cambridge) 2010; 46: 4580

• 139 Song J, Zhang Z, Han B, Hu S, Li W, Xie Y. Green Chem. 2008; 10: 1337

• 140 Zhang S, Huang Y, Jing H, Yao W, Yan P. Green Chem. 2009; 11: 935

• 141 Chang T, Jin L, Jing H. ChemCatChem 2009; 1: 379

• 142 Mizuno T, Nakamura F, Egashira Y, Nishiguchi I, Hirashima T, Ogawa A, Kambe N, Sonoda N. Synthesis 1989; 636

• 143 Mizuno T, Nakai T, Mihara M. Heteroat. Chem. 2010; 21: 99

• 144 Pearson DM, Conley NR, Waymouth RM. Adv. Synth. Catal. 2011; 353: 3007

• 145 Mizuno T, Nakai T, Mihara M. Heteroat. Chem. 2010; 21: 541

• 146 Troisi L, Granito C, Perrone S, Rosato F. Tetrahedron Lett. 2011; 52: 4330

• 147 North M, Omedes-Pujol M. Tetrahedron Lett. 2009; 50: 4452

• 148 Torborg C, Huang J, Schulz T, Schäffner B, Zapf A, Spannenberg A, Börner A, Beller M. Chem.–Eur. J. 2009; 15: 1329

• 149 Blackburn TF, Schwartz J. J. Chem. Soc., Chem. Commun. 1977; 157

• 150 Clements JH. Ind. Eng. Chem. Res. 2003; 42: 663

• 151 Beattie C, North M, Villuendas P. Molecules 2011; 16: 3420

• 152 Su W, Weng Y, Zheng C, Zhang Y, Shi F, Hong B, Chen Z, Li J, Li Z. Org. Prep. Proced. Int. 2009; 41: 93

• 153 Cotarca L, Delogu P, Nardelli A, Šunjic V. Synthesis 1996; 553

• 154 Eckert H, Forster B. Angew. Chem. 1987; 98: 922 Angew. Chem. Int. Ed. Engl. 1987; 26: 894

• 155 Yang F.-Y, Shanmugasundaram M, Chuang S.-Y, Ku P.-J, Wu M.-Y, Cheng C.-H. J. Am. Chem. Soc. 2003; 125: 12 576

• 156 Shiina I, Kubota M, Oshiumi H, Hashizume M. J. Org. Chem. 2004; 69: 1822

• 157 Wei W.-L, Li J.-B, Xin Y, Chang H.-H, Li Y.-W. J. Indian Chem. Soc. 2008; 85: 328

• 158 Yang J, Han X, Zhou L, Xiong C. Asian J. Chem. 2011; 23: 1615

• 159 Marino Jr JP, Osterhout MH, Price AT, Sheehan SM, Padwa A. Tetrahedron Lett. 1994; 35: 849

• 160 Gauthier D, Dodd RH, Dauban P. Tetrahedron 2009; 65: 8542

• 161 Goren Z, Heeg MJ, Mobashery S. J. Org. Chem. 1991; 56: 7186

• 162 Rivero IA, Somanathan R, Hellberg LH. Synth. Commun. 1993; 23: 711

• 163 Encinas L, Chiara JL. J. Comb. Chem. 2008; 10: 361

• 164 Majumdar S, Sloan KB. Synth. Commun. 2006; 36: 3537

• 165 Simila STM, Martin SF. J. Org. Chem. 2007; 72: 5342

• 166 Southgate R. Contemp. Org. Synth. 1994; 1: 417

• 167 Jiao L, Liang Y, Zhang Q, Zhang S, Xu J. Synthesis 2006; 659

• 168 Fernández-Bolaños JG, López Ó, Ulgar VC, Maya I, Fuentes J. Tetrahedron Lett. 2004; 45: 4081

• 169 Ortar G, Cascio MG, De Petrocellis L, Morera E, Rossi F, Schiano-Moriello A, Nalli M, de Novellis V, Woodward DF, Maione S, Di Marzo V. J. Med. Chem. 2007; 50: 6554

• 170 Pevarello P, Brasca MG, Orsini P, Traquandi G, Longo A, Nesi M, Orzi F, Piutti C, Sansonna P, Varasi M, Cameron A, Vulpetti A, Roletto F, Alzani R, Ciomei M, Albanese C, Pastori W, Marsiglio A, Pesenti E, Fiorentini F, Bischoff JR, Mercurio C. J. Med. Chem. 2005; 48: 2944

• 171 Wang Z.-J, Yang J.-G, Yang F, Bao W. Org. Lett. 2010; 12: 3034

• 172 Cantagrel G, de Carné-Carnavalet Bt, Meyer C, Cossy J. Org. Lett. 2009; 11: 4262

• 173 Davis MC, Dahl JEP, Carlson RMK. Synth. Commun. 2008; 38: 1153

• 174 Charalambides YC, Moratti SC. Synth. Commun. 2007; 37: 1037

• 175 Carney DW, Truong JV, Sello JK. J. Org. Chem. 2011; 76: 10 279

• 176 Davies SG, Haggitt JR, Ichihara O, Kelly RJ, Leech MA, Price Mortimer AJ, Roberts PM, Smith AD. Org. Biomol. Chem. 2004; 2: 2630

• 177 Naddo T, Che Y, Zhang W, Balakrishnan K, Yang X, Yen M, Zhao J, Moore JS, Zang L. J. Am. Chem. Soc. 2007; 129: 6978

• 178 Gooßen L, Döhring A. Adv. Synth. Catal. 2003; 345: 943

• 179 Peerlings HWI, Meijer EW. Tetrahedron Lett. 1999; 40: 1021

• 180 Yamamoto Y, Tarbell DS, Fehlner JR, Pope BM. J. Org. Chem. 1973; 38: 2521

• 181 Berger A, Katchalski E. J. Am. Chem. Soc. 1951; 73: 4084

• 182 Nagai A, Sato D, Ishikawa J, Ochiai B, Kudo H, Endo T. Macromolecules 2004; 37: 2332

• 183 Basel Y, Hassner A. J. Org. Chem. 2000; 65: 6368

• 184 Hisada R, Kobayashi M, Minato H. Bull. Chem. Soc. Jpn. 1972; 45: 564

• 185 Bratt MO, Taylor PC. J. Org. Chem. 2003; 68: 5439

• 186 Mamaghani M, Samim HA. Orient. J. Chem. 2008; 24: 837

• 187 Porzelle A, Woodrow MD, Tomkinson NCO. Org. Lett. 2010; 12: 812

• 188 Koley D, Colón OC, Savinov SN. Org. Lett. 2009; 11: 4172

• 189 Drake JE, Yang J. Can. J. Chem. 1998; 76: 319

• 190 El-khateeb M, Asali KJ, Lataifeh A. Polyhedron 2003; 22: 3105

• 191 El-khateeb M, Görls H, Weigand W. Inorg. Chim. Acta 2006; 359: 3985

• 192 Movassagh B, Soleiman-Beigi M. Synth. Commun. 2010; 40: 3467

• 193 Saito Y, Ouchi H, Takahata H. Tetrahedron 2006; 62: 11 599

• 194 Movassagh B, Tavoosi M. Monatsh. Chem. 2008; 139: 251

• 195 Nishiyama Y, Maehira K, Nakase J, Sonoda N. Tetrahedron Lett. 2005; 46: 7415

• 196 Roush WR, Gustin D. Tetrahedron Lett. 1994; 35: 4931

• 197 Reynolds DD, Fields DL, Johnson DL. J. Org. Chem. 1961; 26: 5122

• 198 Hata S, Goto H, Tanaka S, Oku A. J. Appl. Polym. Sci. 2003; 90: 2959

• 199 Kamila S, Khan O, Zhang H, Biehl ER. Synth. Commun. 2006; 36: 1419

• 200 Dash R, Suryawanshi M, Shelke S, Bhosale S, Mahadik K. Med. Chem. Res. 2011; 20: 29

• 201 Nishiyama Y, Katahira C, Sonoda N. Tetrahedron 2006; 62: 5803

• 202 Kumar V, Kaushik MP. Chem. Lett. 2005; 34: 1230

• 203 Torrico-Vallejos S, Erben MF, Ge M.-F, Willner H, Della Védova CO. J. Phys. Chem. A 2010; 114: 3703

• 204 Du L, Yao L, Ge M. Eur. J. Inorg. Chem. 2007; 4514

• 205 Torrico-Vallejos S, Erben MF, Boese R, Della Védova CO. New J. Chem. 2010; 34: 1365

• 206 Torrico-Vallejos S, Erben MF, Willner H, Boese R, Della Védova CO. J. Org. Chem. 2007; 72: 9074

• 207 Torrico-Vallejos S, Erben MF, Boese R, Piro OE, Castellano EE, Della Védova CO. J. Mol. Struct. 2009; 918: 146

• 208 Chaturvedi AK, Chaturvedi D, Mishra N, Mishra V. J. Iran. Chem. Soc. 2010; 7: 702

• 209 Yui K, Aso Y, Otsubo T, Ogura F. Bull. Chem. Soc. Jpn. 1988; 61: 953

• 210 Kikuchi T, Mizukoshi T, Niki T. JP 2002 226 463, 2002 Chem. Abstr.. 2002 137 154930

• 211 Balandier J.-Y, Chas M, Dron PI, Goeb Sb, Canevet D, Belyasmine A, Allain M, Sallé M. J. Org. Chem. 2010; 75: 1589

• 212 Larsen L, Rowe DJ, Garner CD, Joule JA. J. Chem. Soc., Perkin Trans. 1 1989; 2317

• 213 Aitken RA, Mesher STE, Ross FC, Ryan BM. Synthesis 1997; 787

• 214 Barbero M, Degani I, Dughera S, Fochi R, Piscopo L. J. Chem. Soc., Perkin Trans. 1 1996; 289

• 215 Otón F, Lloveras V, Mas-Torrent M, Vidal-Gancedo J, Veciana J, Rovira C. Angew. Chem. 2011; 123: 11 094 Angew. Chem. Int. Ed. 2011; 50: 10 902

• 216 Taguchi Y, Yanagiya K, Shibuya I, Suhara Y. Bull. Chem. Soc. Jpn. 1987; 60: 727

• 217 Taguchi Y, Yanagiya K, Shibuya I, Suhara Y. Bull. Chem. Soc. Jpn. 1988; 61: 921

• 218 Taguchi Y, Yasumoto M, Shibuya I, Suhara Y. Bull. Chem. Soc. Jpn. 1989; 62: 474

• 219 Fournet G, Goré J. Tetrahedron Lett. 1993; 34: 7057

• 220 Bendikov M, Wudl F, Perepichka DF. Chem. Rev. 2004; 104: 4891

• 221 Alberola A, Bosch-Navarro C, Gaviña P, Tatay S. Synth. Met. 2010; 160: 1797

• 222 Trost BM, Waser J, Meyer A. J. Am. Chem. Soc. 2008; 130: 16 424

• 223 Trost BM, Waser J, Meyer A. J. Am. Chem. Soc. 2007; 129: 14 556

• 224 Trost BM, Nguyen HM, Koradin C. Tetrahedron Lett. 2010; 51: 6232

• 225 Narayanaperumal S, Alberto EE, Gul K, Kawasoko CY, Dornelles L, Rodrigues OED, Braga AL. Tetrahedron 2011; 67: 4723

• 226 Tabarelli G, Alberto EE, Deobald AM, Marin G, Rodrigues OED, Dornelles L, Braga AL. Tetrahedron Lett. 2010; 51: 5728

• 227 Marin G, Braga AL, Rosa AS, Galetto FZ, Burrow RA, Gallardo H, Paixão MW. Tetrahedron 2009; 65: 4614

• 228 Fujiwara S.-i, Nishiyama A, Okada K, Maeda H, Shin-ike T, Sonoda N, Kambe N. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 1117

• 229 Sadekov ID, Zakharov AV. Russ. J. Gen. Chem. (Engl. Transl.) 2002; 72: 1586

• 230 Petragnani N, Stefani HA. Tetrahedron 2005; 61: 1613