Abstract
Bismuth is the heaviest stable element of the periodic table and even though it carries the status of heavy metal, it is rated as relatively nontoxic and noncarcinogenic unlike its neighboring elements. Additionally, the fact that it tolerates air and moisture makes the chemistry of bismuth attractive to synthetic chemists. The catalytic nature of this metal is attributed to the capability of its salts to acts as Lewis acids in reactions. The nontoxicity together with the ability to endure moisture makes bismuth compounds favorites of chemists and scientists who are concerned about environmental hazards, and such properties are highly desirable for scale-up of a method. The Lewis acidic nature of salts of this element have been thoroughly investigated in various types of reactions such as cycloaddition reactions, reactions of sugars, protection and deprotection reactions, synthesis of heterocyclic systems etc. Since the 1990s, various research groups have successfully utilized this catalytic nature for many organic transformations. Our group’s contribution towards the development of methodologies that are useful in accomplishing various functional group manipulations by making use of the catalytic properties of bismuth salts is portrayed here. The mechanistic aspects and the catalytic efficiency of the bismuth(III) salts are accented together with the synthetic utility and the biological and pharmacological applications of the methodologies developed.
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References
Komatsu N (2001) In: Suzuki H, Matano Y (eds) Organobismuth chemistry. Elsevier, Amsterdam, pp 371–440, Chapter 5
Postel M, Duñach E (1996) Coord Chem Rev 155:127–144
Suzuki H, Ikegami T, Matanao Y (1997) Synthesis 1997(3):249–267
Nicholas ML, Laura C, Mohan RS (2002) Tetrahedron 58:8373–8397
Le Roux C, Dubac J (2002) Synlett 2002:181–200
Ollevier T, Nadeau E, Desyroy V (2009) Bismuth(III) trifluoromethanesulfonate. In: e-EROS Encyclopedia of Reagents for Organic Synthesis, Wiley, New York. doi: 10.1002/047084289X.rn00959
Smith JG (1984) Synthesis 1984(8):629–656
Posner GH, Rogers DZ (1977) J Am Chem Soc 99:8208–8214
Meguro M, Asao N, Yamamoto Y (1994) J Chem Soc Perkin Trans 1 1994(18):2597–2601
Ollevier T, Lavie-Compin G (2004) Tetrahedron Lett 45:49–52
Ollevier T, Lavie-Compin G (2002) Tetrahedron Lett 43:7891–7893
Ollevier T, Nadeau E (2008) Tetrahedron Lett 49:1546–1550
Pinto RMA, Salvador JAR, Le Roux C (2007) Tetrahedron 63:9221–9228
Li J, Li CJ (2001) Tetrahedron Lett 42:793–796
Yadav JS, Reddy BVS, Venugopal C, Srinivas R, Ramalingam T (2002) Synth Commun 32:1803–1808
Yadav JS, Reddy BVS, Reddy MS (2003) Eur J Org Chem 2003:1779–1783
Ranu BC, Jana U (1998) J Org Chem 63:8212–8216
Viswanathan GS, Yang J, Li CJ (1999) Org Lett 1:993–995
Zhang WC, Viswanathan GS, Li CJ (1999) Chem Commun 1999:291–292
Zhang WC, Li CJ (2000) Tetrahedron 56:2403–2411
Yadav JS, Reddy BVS, Kumar GM, Murthy CVSR (2001) Tetrahedron Lett 42:89–91
Yadav JS, Reddy BVS, Sekhar KC (2001) Synthesis 2001(6):885–888
Keh CCK, Namboodiri VV, Varma RS, Li CJ (2002) Tetrahedron Lett 43:4993–4996
Yadav JS, Reddy BVS, Reddy MS, Niranjan N (2004) J Mol Catal A: Chem 210:99–103
Yadav JS, Rajasekhar K, Murty MSR (2005) Synlett 2005:1945–1947
Yadav JS, Murty MSR, Ram KR (2008) Tetrahedron Lett 49:1141–1145
Petit S, Nallet JP, Guillard M, Dreux J, Chermat R, Poncelet M, Bulach C, Simon P, Fontaine C, Barthelmebs M, Imbs JL (1991) Eur J Med Chem 26:19–32
Zhou Y, Bertolini T, Sun Z, Murphy D, Froelich JM, Webber SE, Hermann T, Wall D (2007) Bioorg Med Chem Lett 17:1206–1210
Ho B, Crider AM, Stables JP (2001) Eur J Med Chem 36:265–286
Watson PS, Jiang B, Scott B (2000) Org Lett 2:3679–3681
Horton DA, Bourne GT, Smythe ML (2003) Chem Rev 103:893–930
Yamamoto Y, Asao N (1993) Chem Rev 93:2207–2293
Ramachandran PV (2002) Aldrichimica Acta 35:23–35
Yadav JS, Reddy BVS, Satheesh G (2003) Tetrahedron Lett 44:6501–6504
Narsaiah AV, Reddy BVS, Premlatha K, Reddy SS, Yadav JS (2009) Catal Letters 131:480–484
Yadav JS, Reddy BVS, Baishya G (2004) Synthesis 2004(11):1854–1858
Maligres PE, See MM, Askin D, Reider PJ (1997) Tetrahedron Lett 38:5253–5256
Wu J, Hou XL, Dai LX (2001) J Chem Soc Perkin Trans 1 2001:1314
Uneyama K, Katagiri T, Takahashi M (1999) J Org Chem 64:7323–7329
Moretti I, Prati F, Antolini L (1997) J Org Chem 62:8784–8789
Ollevier T, Nadeau E (2004) J Org Chem 69:9292–9295
Ollevier T, Nadeau E (2007) Org Biomol Chem 5:3126–3134
Ollevier T, Nadeau E (2006) Synlett 2006:219–222
Srivastava N, Banik BK (2003) J Org Chem 68:2109–2114
Varala R, Alam MM, Adapa SR (2003) Synlett 2003:720–722
Wada M, Takeichi E, Matsumoto T (1991) Bull Chem Soc Jpn 64:990–994
Ollevier T, Bouchard JE, Desyroy V (2008) J Org Chem 73:331–334
Ollevier T, Desyroy V, Debailleul B, Vaur S (2005) Eur J Org Chem 23:4971–4973
Arai K, Yamamoto Y (1990) Chem Pharm Bull 38:2929–2932
Kaji A, Saito R, Kiriyama N (1998) Biol Pharm Bull 21:945–949
Arai K, Shimizu S, Taguchi Y, Yamamoto Y (1981) Chem Pharm Bull 29:991–999
Shimizu S, Yamamoto Y, Koshimura S (1982) Chem Pharm Bull 30:1896–1899
Kaji A, Iwata T, Kiriyama N, Wakusawa S, Miyamoto K (1994) Chem Pharm Bull 42:1682–1684
Alvi KA, Pu H, Luche M, Rice A, App H, McMahon G, Dare H (1999) J Antibiot 52:215–223
Kaji A, Saito R, Nomura M, Miyamoto K, Kiriyama N (1997) Anticancer Res 17:3675–3679
Zhang B, Salituro G, Szalkowski D, Li Z, Zhang Y, Royo I, Vilella D, Diez MT, Pelaez F, Ruby C, Kendall RL, Mao X, Griffin P, Moller DE (1999) Science 284:974–977
Mohlau R, Redlich R (1911) Ber Dtsch Chem Ges 44:3605–3618
Pirrung MC, Park K, Li Z (2001) Org Lett 3:365–367
Pirrung MC, Deng L, Li Z (2002) J Org Chem 67:8374–8388
Yadav JS, Reddy BVS, Swamy T (2003) Tetrahedron Lett 44:9121–9124
Pope FD (1984) J Heterocycl Chem 21:1641–1647
Pajouhesh H, Parsons R, Popp FD (1983) J Pharm Sci 72:318–321
Joshi KC, Pathak VN, Jain SK (1980) Pharmazie 35:677–679
Witkop B, Arvin EK (1951) J Am Chem Soc 73:5664–5669
Seno M, Shiraishri S, Suzuki Y, Asahara T (1978) Bull Chem Soc Jpn 51:1413–1417
Flemming I, Loreto MA, Wallace IHM, Michael JP (1986) J Chem Soc Perkin Trans 1 1986:349–360
Klumpp DA, Yeung KY, Prakash GKS, Olah GA (1998) J Org Chem 59:4481–4484
Yadav JS, Reddy BVS, Gayathri KU, Meraj S, Prasad AR (2006) Synthesis 2006(24):4121–4123
Craig JC, Pearson DE (1971) J Med Chem 14:1221–1222
Johnson JV, Rauckman BS, Baccanari DP (1989) J Med Chem 32:1942–1949
Dillard RD, Pravey DE, Benslay DN (1973) J Med Chem 16:251–253
Theoclitou ME, Robinson LA (2002) Tetrahedron Lett 43:3907–3910
Skraup H (1880) Chem Ber 13:2086
Yadav JS, Reddy BVS, Premalatha K, Murty MSR (2007) J Mol Cat A: Chem 271:161–163
Boger DL, Weinreb SM (1987) Hetero Diels–Alder methodology in organic synthesis. Academic, San Diego
Weinreb SM (1991) Heterodienophile additions to dienes. Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 4. Pergamon, Oxford, pp 401–409
Yamada N, Kadowaki S, Takahashi K, Umezu K (1992) Biochem Pharmacol 44:1211–1213
Faber K, Stueckler H, Kappe T (1984) J Heterocycl Chem 21:1177–1181
Anzini M, Cappelli A, Vomero S, Cagnotto A, Skorupska M (1993) Med Chem Res 3:44–51
Yadav JS, Reddy BVS, Srinivas R (2001) Synth Commun 31:1075–1080
Motorina IA, Grierson DS (1999) Tetrahedron Lett 40:7211–7214
Motorina IA, Grierson DS (1999) Tetrahedron Lett 40:7215–7218
Kiselyov AS, Armstrong RW (1997) Tetrahedron Lett 38:6163
Ma Y, Qian C, Xie M, Sun JJ (1999) J Org Chem 64:6462–6467
Yadav JS, Reddy BVS, Sabitha G (2001) Synthesis 2001(7):10651068
Jones W, Kiselyov AS (2000) Tetrahedron Lett 41:2309–2312
Kiselyov AS, Smith L, Armstrong RW (1998) Tetrahedron 54:5089–5096
Kiselyov AS, Smith LS, Virgilio A, Armstrong RW (1998) Tetrahedron 54:7987
Kiselyov AS, Zhang D (2001) Synlett 2001:1173
Katritzky AR, Rachwal S, Rachwal B (1996) Tetrahedron 52:15031–15070
Carling RW, Leeson PD, Moseley AM, Baker R, Fosteret AC, Grimwood S, Kemp JA, Marshall G (1992) J Med Chem 35:1942–1953
Sabitha G, Reddy EV, Yadav JS, Rama Krishna KSV, Sankar AR (2002) Tetrahedron Lett 43:4029–4032
Sabitha G, Reddy EV, Maruthi C, Yadav JS (2002) Tetrahedron Lett 43:1573–1575
Sabitha G, Reddy EV, Yadav JS (2002) Synthesis 2002(3):409–412
Hoefle G, Steinmetz H, Gerth K, Reichenbach NMH (1991) Liebigs Ann Chem 1991:941–945
Suhara Y, Yamaguchi Y, Collins B, Schnaar RL, Yanagishita M, Hildreth JEK, Shimada I, Ichikawa Y (2002) Bioorg Med Chem 10:1999–2013
Dondoni A, Boscarato A, Marra A (1994) Tetrahedron: Asymmetry 5:2209–2212
Ciccotosto S, von Itzstein M (1995) Tetrahedron Lett 36:5405–5408
Sabesan S, Neira S, Wasserman Z (1995) Carbohydr Res 267:239–261
Snider BB, Hawryluk NA (2000) Org Lett 2:635–638
Yang J, Viswanathan GS, Li CJ (1999) Tetrahedron Lett 40:1627–1630
Yang J, Li CJ (1999) Synlett 1999:717–718
Chan KP, Loh TP (2004) Tetrahedron Lett 45:8387–8390
Sabitha G, Reddy KB, Bhikshapathi M, Yadav JS (2006) Tetrahedron Lett 47:2807–2810
Miranda PO, Diaz DD, Martin VS (2005) J Org Chem 70:57–62
Yadav JS, Reddy BVS, Maity T, Kumar GGKSN (2007) Tetrahedron Lett 48:7155–7159
Yadav JS, Reddy BVS, Maity T, Kumar GGKSN (2007) Tetrahedron Lett 48:8874–8877
Murty MSR, Rajasekhar K, Harikrishna V, Yadav JS (2008) Heteroatom Chem 19:104–106
Sreedhar B, Swapna V, Sridhar C, Saileela D, Sunitha A (2005) Synth Commun 35:1177–1182
Sakata H, Yasukawa H (2003) Jpn Kokai Tokkyo Koho JP 2003121964A:42
Yadav JS, Reddy BVS, Chaya DN, Kumar GGKSN (2008) Can J Chem 86:769–773
Sabitha G, Bhikshapathi M, Yadav JS (2008) Tetrahedron Lett 49:5727–5731
Perron F, Albizati KF (1987) J Org Chem 52:4130–4133
Yadav JS, Reddy BVS, Reddy PN, Rao MS (2003) Synthesis 2003(9):1387–1390
Yadav JS, Reddy BVS, Reddy MS (2004) J Mol Catal A Chem 210:99–103
Yadav JS, Reddy BVS, Reddy PN (2004) Chem Lett 33:1436–1437
Yadav JS, Reddy BVS, Premalatha K (2004) Synlett 2004:963–966
Yadav JS, Reddy BVS, Eeshwaraiah B, Gupta MK (2004) Tetrahedron Lett 45:5873–5876
Yadav JS, Reddy BVS, Premalatha K, Shankar KS (2008) Can J Chem 86:124–128
Lewis MD, Cha JK, Kishi Y (1982) J Am Chem Soc 104:4976–4978
Paterson L, Keown LE (1997) Tetrahedron Lett 38:5727–5730
Horita K, Sakkurai Y, Nagasawa M (1994) Synlett 1994:43–45
Levy DE, Tan C (1995) The chemistry of C-glycosides. Pergamon, Oxford
Du Y, Linhardt RJ (1998) Tetrahedron 54:9913–9959
Nicolaou KC, Duggan ME, Hwang CK (1985) Chem Commun 1985:1359–1361
Mazeas D, Skrydstrup T, Beau JM (1995) Angew Chem Int Ed Engl 34:909–912
Suhadolnik RJ (1970) Nucleoside antibiotics. Wiley Interscience, New York
Hanessian SC (1984) Total synthesis of natural products: the Chiron approach. Pergamon, Oxford
Yadav JS, Reddy BVS, Reddy KS, Chandraiah L, Sunitha V (2004) Synthesis 2004(15):2523–2526
Yadav JS, Reddy BVS, Parimala G, Raju AK (2004) Tetrahedron Lett 45:1543–1545
Stephens JR, Butler PL, Clow CH, Oswald MC, Smith RC, Mohan RS (2003) Eur J Org Chem 2003:3827–3831
Baltork IM, Khosropour AR (2002) Synth Commun 32:2433–2439
Swamy NR, Venkateswarlu Y (2002) Tetrahedron Lett 43:7549–7552
Crouch RD, Romany CA, Kreshock AC, Menconi KA, Zile JL (2004) Tetrahedron Lett 45:1279–1281
Carrigan MD, Eash KJ, Mohan RS (2001) Tetrahedron Lett 42:8133–8135
Leonard NM, Oswald MC, Freiberg DA, Nattier BA, Smith RC, Mohan RS (2002) J Org Chem 67:5202–5207
Carrigan MD, Sarapa D, Smith RC, Wieland LC, Mohan RS (2002) J Org Chem 67:1027–1030
Kamal A, Reddy PSMM, Reddy DR (2003) Tetrahedron Lett 44:2857
Arnold JN, Hayes PD, Kohaus RL, Mohan RS (2003) Tetrahedron Lett 44:9173–9175
Bailey AD, Baru AR, Tasche KK, Mohan RS (2008) Tetrahedron Lett 49:691–694
Navath RS, Pabbisetty KB, Hu L (2006) Tetrahedron Lett 47:389–393
Aggen DH, Arnold JN, Mohan RS (2004) Tetrahedron 60:3675–3679
Cong X, Hu F, Liu KG (2005) J Org Chem 70:4514–4516
Corey EJ, Vekiteshwaralu A (1972) J Am Chem Soc 94:6190–6191
Corey EJ, Snider BB (1972) J Am Chem Soc 94:2549–2550
Sabitha G, Babu RS, Reddy EV, Srividya R, Yadav JS (2001) Adv Synth Catal 343:169–170
Greene TW, Wuts PGM (1999) Protective groups in organic synthesis, 2nd edn. Wiley, New York, p 102
Kocienski PJ (1994) Protecting groups. Thieme, Stuttgart, New York
Dekker CA, Goodman L (1970) In: Pigman W, Horton D (eds) The carbohydrate chemistry and biochemistry (Vol IIA). Academic, New York, pp 22–28
Sabitha G, Reddy EV, Swapna R, Reddy NM, Yadav JS (2004) Synlett 2004:1276–1278
Sabitha G, Babu RS, Reddy EV, Yadav JS (2009) Chem Lett 9:1074–1075
Thomson RH (1987) Naturally occurring quinones, 3rd edn. Academic, New York
Inoue S, Saito K, Kato K (1974) J Chem Soc Perkin Trans 1 1974:2097–2101
Sato K, Inoue S, Saito K (1973) J Chem Soc Perkin Trans 1 1973:2289–2292
Evans DA, Hart DJ, Cain PA, Koelsch PM (1979) Pure Appl Chem 51:1285–1300
Bentley BM, Campbell IM (1979) In: Patai S (ed) The chemistry of quinoid compounds. Wiley, New York, p 683
Hosomi A, Sakurai H (1977) Tetrahedron Lett 18:4041–4044
Ipaktschi J, Heydari A (1992) Angew Chem Int Ed Engl 31:313–314
Araki S, Katsumura N, Butsugan Y (1992) J Organomet Chem 415:7–24
Hegedus LS, Evans BR, Korte DE, Waterman EL, Sjoberg K (1976) J Am Chem Soc 101:3901–3909
Fisher A, Henderson GN (1980) Tetrahedron Lett 21:701–704
Evans DA, Hoffmann JM (1976) J Am Chem Soc 98:1983–1986
Naruta Y (1980) J Am Chem Soc 102:3774–3783
Takuwa A, Soga O, Mishima T, Maruyama K (1987) J Org Chem 52:1261–1265
Yadav JS, Reddy BVS, Swamy T (2003) Tetrahedron Lett 44:4861–4864
Yadav JS, Reddy BVS, Swamy T, Rao KR (2004) Tetrahedron Lett 45:6037–6039
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Yadav, J.S., Antony, A., Reddy, B.V.S. (2011). Bismuth(III) Salts as Synthetic Tools in Organic Transformations. In: Ollevier, T. (eds) Bismuth-Mediated Organic Reactions. Topics in Current Chemistry, vol 311. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_274
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