4.3. 15 Bismuth Compounds (Update 2018)
Book
Editors: Banert, K.; Clarke, P. A.; Drabowicz, J.; Oestreich, M.
Title: Knowledge Updates 2018/4
Print ISBN: 9783132423251; Online ISBN: 9783132423282; Book DOI: 10.1055/b-006-161209
1st edition © 2019 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
This chapter is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of organobismuth compounds and their use in organic synthesis. Organobismuth compounds are organometallic species that contain a carbon-bismuth bond. These species have been used as catalysts and reagents in various reactions that lead to the formation of carbon-carbon, carbon-nitrogen, carbon-oxygen, carbon-sulfur, and carbon-selenium bonds.
Key words
arylation - bismuth compounds - carbon-metal bonds - copper catalysts - cross-coupling reactions - heterocycles - organometallic reagents - palladium catalysts - transition metals- 2 Berger RJF, Rettenwander D, Spirk S, Wolf C, Patzschke M, Ertl M, Monkowius U, Mitzel NW. Phys. Chem. Chem. Phys. 2012; 14: 15 520
- 8 Murafuji T, Azuma T, Miyoshi Y, Ishibashi M, Rahman AFMM, Migita K, Sugihara Y, Mikata Y. Bioorg. Med. Chem. Lett. 2006; 16: 1510
- 9 Kotani T, Nagai D, Asahi K, Suzuki H, Yamao F, Kataoka N, Yagura T. Antimicrob. Agents Chemother. 2005; 49: 2729
- 10 Murafuji T, Fujiwara Y, Yoshimatsu D, Miyakawa I, Migita K, Mikata Y. Eur. J. Med. Chem. 2011; 46: 519
- 12 Yang Y, Ouyang R, Xu L, Guo N, Li W, Feng K, Ouyang L, Yang Z, Zhou S, Miao Y. J. Coord. Chem. 2015; 68: 379
- 17 Yamago S, Kayahara E, Kotani M, Ray B, Kwak Y, Goto A, Fukuda T. Angew. Chem. Int. Ed. 2007; 46: 1304
- 40 Matsumura M, Shibata K, Ozeki S, Yamada M, Murata Y, Kakusawa N, Yasuike S. Synthesis 2016; 48: 730
- 41 Hébert M, Petiot P, Benoit E, Dansereau J, Ahmad T, Le Roch A, Ottenwaelder X, Gagnon A. J. Org. Chem. 2016; 81: 5401
- 55 Ahmad T, Dansereau J, Hébert M, Grand-Maître C, Larivée A, Siddiqui A, Gagnon A. Tetrahedron Lett. 2016; 57: 4284
- 62 Lemus A, Sharma P, Cabrera A, Rosas N, Alvarez C, Gomez E, Sharma M, Cespededs C, Hernandez S. Main Group Met. Chem. 2001; 24: 835
- 63 Sharma P, Rosas N, Cabrera A, Hernandez MJS, Toscano A, Hernández S, Gutierrez R. Appl. Organomet. Chem. 2005; 19: 1121
- 64 Sharma P, Rosas N, Cabrera A, Toscano A, de Jesus Silva M, Perez D, Velasco L, Perez J, Gutierez R. J. Organomet. Chem. 2005; 690: 3286
- 70 Obata T, Matsumura M, Kawahata M, Hoshino S, Yamada M, Murata Y, Kakusawa N, Yamaguchi K, Tanaka M, Yasuike S. J. Organomet. Chem. 2016; 807: 17
- 76 Urgin K, Aubé C, Pichon C, Pipelier M, Blot V, Thobie-Gautier C, Léonel E, Dubreuil D, Condon S. Tetrahedron Lett. 2012; 53: 1894
- 78 Tyrra W, Naumann D, Kirij NV, Kolomeitsev AA, Yagupolskii YL. J. Chem. Soc., Dalton Trans. 1999; 657
- 85 Preda AM, Schneider WB, Rainer M, Rüffer T, Schaarschmidt D, Lang H, Mehring M. Dalton Trans. 2017; 46: 8269
- 86 Preda AM, Schneider WB, Schaarschmidt D, Lang H, Mertens L, Auer AA, Mehring M. Dalton Trans. 2017; 46: 13 492
- 87 Auer AA, Mansfeld D, Nolde C, Schneider W, Schürmann M, Mehring M. Organometallics 2009; 28: 5405
- 91 Breunig HJ, Haddad N, Lork E, Mehring M, Mügge C, Nolde C, Raţ CI, Schürmann M. Organometallics 2009; 28: 1202
- 93 Zhang X.-W, Xia J, Yan H.-W, Luo S.-L, Yin S.-F, Au C.-T, Wong W.-Y. J. Organomet. Chem. 2009; 694: 3019
- 98 Peveling K, Schürmann M, Herres-Pawlis S, Silvestru C, Jurkschat K. Organometallics 2011; 30: 5181
- 102 Breunig HJ, Königsmann L, Lork E, Nema M, Philipp N, Silvestru C, Soran A, Varga RA, Wagner R. Dalton Trans. 2008; 1831
- 103 Zhang X, Yin S, Qiu R, Xia J, Dai W, Yu Z, Au C.-T, Wong W.-Y. J. Organomet. Chem. 2009; 694: 3559
- 104 Qiu R, Meng Z, Yin S, Song X, Tan N, Zhou Y, Yu K, Xu X, Luo S, Au C.-T, Wong W.-Y. ChemPlusChem 2012; 77: 404
- 105 Andrews PC, Ferrero RL, Forsyth CM, Junk PC, MacLellan JG, Peiris RM. Organometallics 2011; 30: 6283
- 107 Andrews PC, Busse M, Deacon GB, Ferrero RL, Junk PC, Huynh KK, Kumara I, MacLellan JG. Dalton Trans. 2010; 39: 9633
- 108 Murafuji T, Kitagawa K, Yoshimatsu D, Kondo K, Ishiguro K, Tsunashima R, Miyakawa I, Mikata Y. Eur. J. Med. Chem. 2013; 63: 531
- 114 Dostál L, Novák P, Jambor R, Růžička A, Císařová I, Jirásko R, Holeček J. Organometallics 2007; 26: 2911
- 115 Gupta A, Sharma RK, Bohra R, Jain VK, Drake JE, Hursthouse MB, Light ME. J. Organomet. Chem. 2003; 678: 122
- 121 Dostál L, Jambor R, Růžička A, Jirásko R, Černošková E, Beneš L, de Proft F. Organometallics 2010; 29: 4486
- 123 Chovancová M, Jambor R, Růžička A, Jirásko R, Císařová I, Dostál L. Organometallics 2009; 28: 1934
- 130 Metre RK, Kundu S, Narayanan RS, Chandrasekhar V. Phosphorus, Sulfur Silicon Relat. Elem. 2015; 190: 2134
- 132 Beckmann J, Bolsinger J, Duthie A, Finke P, Lork E, Lüdtke C, Mallow O, Mebs S. Inorg. Chem. 2012; 51: 12 395
- 138 Svoboda T, Jambor R, Růžička A, Jirásko R, Lyčka A, De Proft F, Dostál L. Organometallics 2012; 31: 1725
- 139 Fridrichová A, Svoboda T, Jambor R, Padělková Z, Růžička A, Erben M, Jirásko R, Dostál L. Organometallics 2009; 28: 5522
- 140 Heimann S, Kuczkowski A, Bläser D, Wölper C, Haack R, Jansen G, Schulz S. Eur. J. Inorg. Chem. 2014; 4858
- 155 Sasamori T, Arai Y, Takeda N, Okazaki R, Furukawa Y, Kimura M, Nagase S, Tokitoh N. Bull. Chem. Soc. Jpn. 2002; 75: 661
- 156 Sasamori T, Mieda E, Nagahora N, Takeda N, Takagi N, Nagase S, Tokitoh N. Chem. Lett. 2005; 34: 166
- 169 Braunschweig H, Brenner P, Cogswell P, Kraft K, Schwab K. Chem. Commun. (Cambridge) 2010; 46: 7894
- 174 Breunig HJ, Borrmann T, Lork E, Moldovan O, Raţ CI, Wagner RP. J. Organomet. Chem. 2009; 694: 427
- 185 Becker E, Slugovc C, Rüba E, Standfest-Hauser C, Mereiter K, Schmid R, Kirchner K. J. Organomet. Chem. 2002; 649: 55
- 189 Tschersich C, Limberg C, Roggan S, Herwig C, Ernsting N, Kovalenko S, Mebs S. Angew. Chem. Int. Ed. 2012; 51: 4989
- 198 Barton DHR, Bhatnagar NY, Blazejewski J.-C, Charpiot B, Finet J.-P, Lester DJ, Motherwell WB, Barros Papoula MT, Stanforth SP. J. Chem. Soc., Perkin Trans. 1 1985; 2657
- 199 Barton DHR, Yadav-Bhatnagar N, Finet J.-P, Khamsi J, Motherwell WB, Stanforth SP. Tetrahedron 1987; 43: 323
- 214 Islam A, Lages Rodrigues B, Marques Marzano I, Perreira-Maia EC, Dittz D, Paz Lopes MT, Ishfaq M, Frézard F, Demicheli C. Eur. J. Med. Chem. 2016; 109: 254
- 222 Matano Y, Aratani Y, Miyamatsu T, Kurata H, Miyaji K, Sasako S, Suzuki H. J. Chem. Soc., Perkin Trans. 1 1998; 2511
- 224 Rahman AFMM, Murafuji T, Ishibashi M, Miyoshi Y, Sugihara Y. J. Organomet. Chem. 2004; 689: 3395
- 228 Egorova IV, Zhidkov VV, Grinishak IP, Rezvanova AA. Russ. J. Gen. Chem. (Engl. Transl.) 2014; 84: 1374
- 233 Bolshakov AV, Ganina OG, Shavirin AS, Kurskii YA, Finet J.-P, Fedorov AY. Tetrahedron Lett. 2002; 43: 8245
- 237 Sharutin VV, Senchurin VS, Sharutina OK, Bregadze VI, Zhigareva GG. Russ. J. Gen. Chem. (Engl. Transl.) 2010; 80: 1941
- 239 Sharutin VV, Egorova IV, Sharutina OK, Ivanenko TK, Gatilov YV, Adonin NA, Starichenko VF. Russ. J. Coord. Chem. (Engl. Transl.) 2003; 29: 462
- 240 Andreev PV, Somov NV, Kalistratova OS, Gushchin AV, Chuprunov EV. Crystallogr. Rep. 2015; 60: 517
- 241 Moiseev DV, Malysheva YB, Shavyrin AS, Kurskii YA, Gushchin AV. J. Organomet. Chem. 2005; 690: 3652
- 246 Sharutin VV, Egorova IV, Sharutina OK, Pakusina AP, Pushilin MA. Russ. J. Coord. Chem. (Engl. Transl.) 2007; 33: 12
- 251 Sharutin VV, Sharutina OK, Egorova IV, Ivanenko TK, Bel’skii VK. Russ. J. Gen. Chem. (Engl. Transl.) 2002; 72: 44
- 252 Barton DHR, Kitchin JP, Lester DJ, Motherwell WB, Barros Papoula MT. Tetrahedron, Suppl. 1981; 37: 73
- 256 Feham K, Benkadari A, Chouaih A, Miloudi A, Boyer G, El Abed D. Cryst. Struct. Theory Appl. 2013; 2: 28
- 282 Sharutin VV, Egorova IV, Tsiplukhina TV, Gerasimenko AV, Pushilin MA. Russ. J. Coord. Chem. (Engl. Transl.) 2004; 30: 884
- 287 Vránová I, Alonso M, Lo R, Sedlák R, Jambor R, Růžička A, De Proft F, Hobza P, Dostál L. Chem.–Eur. J. 2015; 21: 16 917
- 290 Qiu R, Qiu Y, Yin S, Xu X, Luo S, Au C.-T, Wong W.-Y, Shimada S. Adv. Synth. Catal. 2010; 352: 153
- 291 Qiu R, Qiu Y, Meng Z, Song X, Jia Z, Yu K, Yin S, Au C.-T, Wong W.-Y. Adv. Mater. Phys. Chem. 2012; 2: 142
- 292 Qiu R, Qiu Y, Yin S, Song X, Meng Z, Xu X, Zhang X, Luo S, Au C.-T, Wong W.-Y. Green Chem. 2010; 12: 1767
- 294 Tan N, Yin S, Li Y, Qiu R, Meng Z, Song X, Luo S, Au C.-T, Wong W.-Y. J. Organomet. Chem. 2011; 696: 1579
- 308 Barton DHR, Barros Papoula MT, Guilhem J, Motherwell WB, Pascard C, Huu Dau ET. J. Chem. Soc., Chem. Commun. 1982; 732
- 310 Barton DHR, Blazejewski J.-C, Charpiot B, Lester DJ, Motherwell WB, Barros Papoula MT. J. Chem. Soc., Chem. Commun. 1980; 827
- 321 Petiot P, Dansereau J, Hébert M, Khene I, Ahmad T, Samaali S, Leroy M, Pinsonneault F, Legault CY, Gagnon A. Org. Biomol. Chem. 2015; 13: 1322
- 322 Pietri S, Liebgott T, Finet J.-P, Culcasi M, Billottet L, Bernard-Henriet C. Drug Dev. Res. 2001; 54: 191
- 323 Sinclair PJ, Wong F, Staruch MJ, Wiederrecht G, Parsons WH, Dumont F, Wyvratt M. Bioorg. Med. Chem. Lett. 1996; 6: 2193
- 343 Barton DHR, Blazejewski J.-C, Charpiot B, Finet J.-P, Motherwell WB, Barros Papoula MT, Stanforth SP. J. Chem. Soc., Perkin Trans. 1 1985; 2667
- 356 Kutudila P, Linguerri R, Al-Mogren MM, Pichon C, Condon S, Hochlaf M. Theor. Chem. Acc. 2016; 135: 176
- 360 Monguchi Y, Hattori T, Miyamoto Y, Yanase T, Sawama Y, Sajiki H. Adv. Synth. Catal. 2012; 354: 2561
- 363 Paluru DK, Dey S, Chaudhari KR, Khedkar MV, Bhanage BM, Jain VK. Tetrahedron Lett. 2014; 55: 2953
- 366 Urgin K, Aubé C, Pipelier M, Blot V, Thobie-Gautier C, Sengmany S, Lebreton J, Léonel E, Dubreuil D, Condon S. Eur. J. Org. Chem. 2013; 117
- 375 Stammers TA, Coulombe R, Duplessis M, Fazal G, Gagnon A, Garneau M, Goulet S, Jakalian A, LaPlante S, Rancourt J, Thavonekham B, Wernic D, Kukolj G, Beaulieu P. Bioorg. Med. Chem. Lett. 2013; 23: 6879
- 384 Shimada S, Yamazaki O, Tanaka T, Rao MLN, Suzuki Y, Tanaka M. Angew. Chem. Int. Ed. 2003; 42: 1845
- 407 Malysheva YB, Gushchin AV, Mei Y, Lu Y, Ballauff M, Proch S, Kempe R. Eur. J. Inorg. Chem. 2008; 379
- 409 Matsumura M, Yamada M, Tsuji T, Murata Y, Kakusawa N, Yasuike S. J. Organomet. Chem. 2015; 794: 70
- 420 Gushchin AV, Malysheva YB, Kosov DY, Sharutin VV. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 1253
- 421 Gushchin AV, Malysheva YB, Kosov DY, Sharutin VV. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 1249
- 422 Malysheva YB, Moiseev DV, Gushchin AV, Dodonov VA. Russ. J. Gen. Chem. (Engl. Transl.) 2005; 75: 1766