Mono- and biscouplings using triarylbismuths for the atom-efficient arylations of functionalized furans under palladium catalysis

Synlett

Volumn 23, Issue 13, 2012, Pages 1907-1912

  Rao, Maddali L N ^a   Awasthi, Dheeraj K ^a   Talode, Jalindar B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

2 bromofurans; arylation; cross coupling; palladium; triarylbismuths

Indexed keywords

2 ARYLFURAN DERIVATIVE; 2,5 DIBROMOFURAN DERIVATIVE; CHEMICAL COMPOUND; FURAN DERIVATIVE; PALLADIUM; TRIARYLBISMUTH DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; ISOMERIZATION; POLYMERIZATION; REACTION TIME; SYNTHESIS;

EID: 84864060874     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316567     Document Type: Article

References (58)

1. Lipshutz BH. Chem. Rev.: 1986; 86 795
2. Chiarello J, Joullie MM. Tetrahedron: 1988; 44 41
3. Hashmi A.S. K, Enns E, Frost TM, Schafer S, Frey W, Rominger F. Synthesis: 2008; 2707
4. Antonioletti R, D'Auria M, De Mico A, Piancatelli G, Scettri A. Tetrahedron: 1985; 41 3441
5. Crawford KR, Bur SK, Straub CS, Padwa A. Org. Lett.: 2003; 5 3337
6. Martin-Matute B, Nevado C, Cardenas DJ, Echavarren AM. J. Am. Chem. Soc.: 2003; 125 5757
7. Hough LB, Menge W.M. P. B, van de Stolpe AC, Nalwalk JW, Leurs R, de Esch IJ. P. Bioorg. Med. Chem. Lett.: 2007; 17 5715
8. Ramalingan C, Lee I.-S, Kwak Y.-W. Chem. Pharm. Bull.: 2009; 57 591
9. Ismail MA, Brun R, Wenzler T, Tanious FA, Wilson WD, Boykin DW. J. Med. Chem.: 2004; 47 3658
10. Hosoya T, Aoyama H, Ikemoto T, Kihara Y, Hiramatsu T, Endo M, Suzuki M. Bioorg. Med. Chem.: 2003; 11 663
11. Zhang J, Pettersson HI, Huitema C, Niu C, Yin J, James M.N. G, Eltis LD, Vederas JC. J. Med. Chem.: 2007; 50 1850
12. Moreau F, Desroy N, Genevard JM, Vongsouthi V, Gerusz V, Le Fralliec G, Oliveira C, Floquet S, Denis A, Escaich S, Wolf K, Busemann M, Aschenbrenner A. Bioorg. Med. Chem. Lett.: 2008; 18 4022
13. Urbano M, Guerrero M, Zhao J, Velaparthi S, Schaeffer M.-T, Brown S, Rosen H, Roberts E. Bioorg. Med. Chem. Lett.: 2011; 21 5470
14. Paquette LA, Efremov I. J. Am. Chem. Soc.: 2001; 123 4492
15. Woo CH, Beaujuge PM, Holocombe TW, Lee OP, Frechet J.M. J. J. Am. Chem. Soc.: 2010; 132 15547
16. Lin JT, Chen P.-C, Yen Y.-S, Hsu Y.-C, Chou H.-H, Yeh M.-CP. Org. Lett.: 2009; 11 97
17. Umezawa K, Matsui A, Nakamura Y, Citterio D, Suzuki K. Chem.-Eur. J.: 2009; 15 1096
18. Schroter S, Stock C, Bach T. Tetrahedron: 2005; 61 2245
19. Billingsley K, Buchwald SL. J. Am. Chem. Soc.: 2007; 129 3358
20. Ismail MA, Boykin DW, Stephens CE. Tetrahedron Lett.: 2006; 47 795
21. Molander GA, Ellis N. Acc. Chem. Res.: 2007; 40 275
22. Denmark SE, Sweis RF. Acc. Chem. Res.: 2002; 35 835
23. Denmark SE, Regens CS. Acc. Chem. Res.: 2008; 41 1486
24. Lee K, Lee PH. Tetrahedron Lett.: 2008; 49 4302
25. Jain P, Ferrence GM, Lash TD. J. Org. Chem.: 2010; 75 6563
26. Haag BA, Samann C, Jana A, Knochel P. Angew. Chem. Int. Ed.: 2011; 50 7290
27. Kondolff I, Doucet H, Santelli M. J. Mol. Catal. A: Chem.: 2007; 269 110
28. Feuerstein M, Doucet H, Santelli M. Tetrahedron Lett.: 2001; 42 5659
29. Milkiewicz KL, Parks DJ, Lu T. Tetrahedron Lett.: 2003; 44 4257
30. Bussolari JC, Rehborn DC. Org. Lett.: 1999; 1 965
31. Raheem M.-A, Nagireddy JR, Durham R, Tam W. Synth. Commun.: 2010; 40 2138
32. Gong Y, Pauls HW. Synlett: 2000; 829
33. Fisera L, Kovac J, Komanova E. Tetrahedron: 1974; 30 4123
34. Antonioletti R, D'Auria M, D'Onofrio F, Piancatelli G, Scettri A. J. Chem. Soc., Perkin Trans. 1: 1986; 1755
35. Liegault B, Lapointe D, Caron L, Vlassova A, Fagnou K. J. Org. Chem.: 2009; 74 1826
36. Dong JJ, Roger J, Pozgan F, Doucet H. Green Chem.: 2009; 11 1832
37. Palmieri A, Gabrielli S, Ballini R. Chem. Commun.: 2010; 46 6165
38. Parry PR, Bryce MR, Tarbit B. Org. Biomol. Chem.: 2003; 1 1447
39. McClure MS, Roschangar F, Hodson SJ, Millar A, Osterhout MH. Synthesis: 2001; 1681
40. Takahashi K, Gunji A, Yanagi K, Miki M. Tetrahedron Lett.: 1995; 36 8055
41. Kim S.-H, Rieke RD. Tetrahedron Lett.: 2010; 51 2657
42. Rieke RD, Kim S.-H. Tetrahedron Lett.: 2011; 52 1128
43. Gauthier D.R. Jr, Szumigala RH, Dormer PG, Armstrong JD. III, Volante RP, Reider PJ. Org. Lett.: 2002; 4 375
44. Botteselle GV, Hough T.L. S, Venturoso RC, Cella R, Vieira AS, Stefani AS, Stefani HA. Aust. J. Chem.: 2008; 61 870
45. Stephens CE, Tanious F, Kim S, Wilson WD, Schell WA, Perfect JR, Franzblau SG, Boykin DW. J. Med. Chem.: 2001; 44 1741 and references cited therein
46. Ishida H, Yui K, Aso Y, Otsubo T, Ogura F. Bull. Chem. Soc. Jpn.: 1990; 63 2828
47. Rao M.L. N, Jadhav DN, Banerjee D. Tetrahedron: 2008; 64 5762
48. Rao M.L. N, Banerjee D, Jadhav DN. Tetrahedron Lett.: 2007; 48 2707
49. Rao M.L. N, Banerjee D, Jadhav DN. Tetrahedron Lett.: 2007; 48 6644
50. Feuerstein M, Doucet H, Santelli M. J. Organomet. Chem.: 2003; 687 327
51. Molander GA, Sandrock DL. Org. Lett.: 2007; 9 1597
52. Sato K, Ikeda K, Suzuki T, Aoyama S, Maki N, Suzuki Y, Sato M. Tetrahedron: 2007; 63 7571
53. Karpov AS, Rominger F, Müller T.J. J. J. Org. Chem.: 2003; 68 1503
54. Trost BM, Weiss AH. Org. Lett.: 2006; 8 4461
55. Gung BW, Dickson H, Shockley S. Tetrahedron Lett.: 2001; 42 4761
56. Garcia J, Lopez M, Romeu J. Synlett: 1999; 429
57. Franz AW, Popa LN, Rominger F, Müller T.J. J. Org. Biomol. Chem.: 2009; 7 469
58. Agapie T, Henling LM, DiPasquale AG, Rheingold AL, Bercaw JE. Organometallics: 2008; 27 6245