FeF3/i2-catalyzed synthesis of 4-chalcogen- substituted arylamines by direct thiolation of an arene C-H bond

Synthesis

Volumn , Issue 7, 2011, Pages 1099-1105

  Fang, Xiao Li ^a   Tang, Ri Yuan ^a   Zhang, Xing Guo ^a   Li, Jin Heng ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

4 chalcogen substituted arylamine; arylamine; iodine; iron; selenation; sulfenylation

Indexed keywords

ARYL AMINES; C-H BOND; CATALYZED SYNTHESIS; CHALCOGENS; DISELENIDES; GOOD YIELD; REGIOSELECTIVE SYNTHESIS; SELENATION; SULFENYLATION; THIOLATION;

CATALYSIS; INDUSTRIAL CHEMICALS; IODINE; SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

2 CHLORO 4 (PHENYLTHIO)ANILINE; 2 CHLORO 5 METHOXY 4 (PHENYLTHIO)ANILINE; 2 METHOXY 4 (PHENYLTHIO)ANILINE; 2 METHYL 4 (PHENYLTHIO)ANILINE; 2,6 DIMETHYL 4 (PHENYLTHIO)ANILINE; 3 METHYL 4 (PHENYLTHIO)ANILINE; 4 (4 FLUOROPHENYLTHIO)ANILINE; 4 (4 NITROPHENYLTHIO)ANILINE; 4 (4 TOLYTHIO)ANILINE; 4 (METHYLSELANYL)ANILINE; 4 (METHYLTHIO)ANILINE; 4 (PHENYLSELANYL)ANILINE; 4 (PHENYLTHIO)ANILINE; 4 (PYRIDIN 2 YLTHIO)ANILINE; 4 CHALCOGEN ARYLAMINE DERIVATIVE; 4 METHOXY 2 (PHENYLTHIO)ANILINE; 4 METHYL 2 (PHENYLTHIO)ANILINE; ANILINE DERIVATIVE; AROMATIC AMINE; CARBON; FERRIC ION; HYDROGEN; IODINE DERIVATIVE; MESITYL(PHENYL)SULFIDE; N METHYL 4 (PHENYLTHIO)ANILINE; PHENYL(2,4,6 TRIMETHOXYPHENYL)SULFIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION KINETICS; HYDROGEN BOND; SELENATION; STEREOCHEMISTRY; SULFENYLATION; SYNTHESIS; THIOLATION;

EID: 79953024673     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258449     Document Type: Article

References (82)

1. Liu G, Huth J R., Olejniczak E T., Mendoza R, DeVries P, Leitza S, Reilly E B., Okasinski G F., Fesik S W., von Geldern T W., J. Med. Chem. 2001 44 1202
2. De Martino G, Edler M C., La Regina G, Coluccia A, Barbera M C., Barrow D, Nicholson R I., Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R, J. Med. Chem. 2006 49 947
3. Nose M, Suzuki H, Synthesis 2002 1065
4. Sousa S C. A., Fernandes A C., Tetrahedron Lett. 2009 50 6872
5. Khurana J M., Sharma V, Chako S A., Tetrahedron 2007 63 966
6. Bahrami K, Khodaei M M., Karimi A, Synthesis 2008 2543
7. For reviews, see:, Kondo T, Mitsudo T, Chem. Rev. 2000 100 3205
8. Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 42 5400
9. Hartwig J F., Acc. Chem. Res. 2008 41 1534
10. Kunz K, Scholz U, Ganzer D, Synlett 2003 2428
11. For selected papers on Pd-catalyzed C-S coupling reactions, see:, Fernández-Rodriguez M A., Hartwig J F., J. Org. Chem. 2009 74 1663
12. Murata M, Buchwald S L., Tetrahedron 2004 60 7397
13. Schopfer U, Schlapbach A, Tetrahedron 2001 57 3069
14. Li G Y., Angew. Chem. Int. Ed. 2001 40 1513
15. Moreau X, Campagne J M., Meyer G, Jutand A, Eur. J. Org. Chem. 2005 3749
16. Li G Y., Zheng G, Noonan A F., J. Org. Chem. 2001 66 8677
17. For selected papers on copper-catalyzed C-S coupling reactions, see:, Kabir M S., Lorenz M, Van Linn M L., Namjoshi O A., Ara S, Cook J M., J. Org. Chem. 2010 75 3626
18. Kwong F Y., Buchwald S L., Org. Lett. 2002 4 3517
19. Wu Y.-J, He H, Synlett 2003 1789
20. Chen Y.-J, Chen H.-H, Org. Lett. 2006 8 5609
21. Zhu D, Xu L, Wu F, Wan B S., Tetrahedron Lett. 2006 47 5781
22. Herrero M T., San Martin R, Domínguez E, Tetrahedron 2009 65 1500
23. Buranaprasertsuk P, Chang J W. W., Chavasiri W, Chan P W. H., Tetrahedron Lett. 2008 49 2023
24. Lv X, Bao W, J. Org. Chem. 2007 72 3863
25. Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T, J. Org. Chem. 2009 74 1971
26. Fernandez Rodríguez M A., Shen Q, Hartwig J F., J. Am. Chem. Soc. 2006 128 2180
27. Mispelaere-Canivet C, Spindler J.-F, Perrio S, Beslin P, Tetrahedron 2005 61 5253
28. Itoh T, Mase T, Org. Lett. 2004 6 4587
29. Zheng N, McWilliams J C., Fleitz F J., Armstrong J D., Volante R P., J. Org. Chem. 1998 63 9606
30. Eichman C C., Stambuli J P., J. Org. Chem. 2009 74 4005
31. Correa A, Carril M, Bolm C, Angew. Chem. Int. Ed. 2008 47 2880
32. Reddy V P., Kumar A V., Swapna K, Rao K R., Org. Lett. 2009 11 1697
33. Nakamura I, Sato T, Yamamoto Y, Angew. Chem. Int. Ed. 2006 45 4473
34. Taniguchi N, J. Org. Chem. 2007 72 1241
35. Taniguchi N, J. Org. Chem. 2004 69 6904
36. Taniguchi N, Onami T, Synlett 2003 829
37. Taniguchi N, Onami T, J. Org. Chem. 2004 69 915
38. G ómez-Benítez V, Baldovino-Pantaleón O, Herrera-Álvarez C, Toscano R A., Morales-Morales D, Tetrahedron Lett. 2006 47 5059
39. Kumar S, Engman L, J. Org. Chem. 2006 71 5400
40. Baldovino-Pantaleón O, Hernandez-Ortega S, Morales-Morales D, Adv. Synth. Catal. 2006 348 236
41. Fukuzawa S.-i, Tanihara D, Kikuchi S, Synlett 2006 2145
42. Takeuchi H, Hiyama T, Kamai N, Oya H, J. Chem. Soc., Perkin Trans. 2 1997 2301
43. Takeuchi H, Suga K, J. Chem. Soc., Perkin Trans. 2 2000 1803
44. For selected recent reviews, see:, Dyker G, Handbook of C-H Transformations. Applications in Organic Synthesis Wiley-VCH Weinheim 2005
45. Colby D A., Bergman R G., Ellman J A., Chem. Rev. 2010 110 624
46. Lyons T W., Sanford M S., Chem. Rev. 2010 110 1147
47. Mkhalid I A., Barnard J H., Marder T B., Murphy J M., Hartwig J F., Chem. Rev. 2010 110 890
48. Zhang M, Adv. Synth. Catal. 2009 351 2243
49. Mori A, Sugie A, Bull. Chem. Soc. Jpn. 2008 81 548
50. Diaz-Requejo M M., Pérez P J., Chem. Rev. 2008 108 3379
51. Chu L, Yue X, Qing F.-L, Org. Lett. 2010 12 1644
52. Zhao X, Dimitrijevic E, Dong V M., J. Am. Chem. Soc. 2009 131 3466
53. Fukuzawa S.-i, Shimizu E, Atsuumi Y, Haga M, Ogata K, Tetrahedron Lett. 2009 50 2374
54. Joyce L L., Batey R A., Org. Lett. 2009 11 2792
55. Inamoto K, Hasegawa C, Hiroya K, Doi T, Org. Lett. 2008 10 5147
56. Chen X, Hao X.-S, Goodhue C E., Yu J.-Q, J. Am. Chem. Soc. 2006 128 6790
57. Ranken P F., McKinnie G B., J. Org. Chem. 1989 54 2985
58. Yadav J S., Reddy B V. S., Reddy Y J., Praneeth K, Synthesis 2009 1520
59. Fang X L., Tang R Y., Zhong P, Li J H., Synthesis 2009 4183
60. Tang R.-Y, Zhong P, Lin Q.-L, J. Fluorine Chem. 2006 127 948
61. Tang R.-Y, Zhong P, Lin Q.-L, Synlett 2007 85
62. Wang Z.-L, Tang R.-Y, Luo P.-S, Deng C.-L, Zhong P, Li J.-H, Tetrahedron 2008 64 10670
63. Luo P.-S, Yu M, Tang R.-Y, Zhong P, Li J.-H, Tetrahedron Lett. 2009 50 1066
64. Luo P.-S, Wang F, Li J.-H, Tang R.-Y, Zhong P, Synthesis 2009 921
65. Guo Y.-J, Tang R.-Y, Li J.-H, Zhong P, Zhang X.-G, Adv. Catal. Synth. 2009 351 2615
66. Waterson A G., Petrov K G., Hornberger K R., Hubbard R D., Sammond D M., Smith S C., Dickson H D., Caferro T R., Hinkle K W., Stevens K L., Dickerson S H., Rusnak D W., Spehar G M., Wood E R., Griffin R J., Uehling D E., Bioorg. Med. Chem. Lett. 2009 19 1332
67. Seto M, Miyamoto N, Aikawa K, Aramaki Y, Kanzaki N, Iizawa Y, Baba M, Shiraishi M, Bioorg. Med. Chem. 2004 13 363
68. Delarge J, Thunus L, Beckers C, Ghys A, Denef J, Jamoulle J C., Eur. J. Med. Chem. 1984 19 559
69. Fujisawa T, Kojima T, J. Org. Chem. 1973 38 687
70. Wong Y.-C, Jayanth T T., Cheng C.-C, Org. Lett. 2006 8 5613
71. Marcincal-Lefebvre A, J. Med. Chem. 1981 24 889
72. Zhang Y, Org. Lett. 2007 9 3495
73. Moore M L., J. Am. Chem. Soc. 1935 57 1517
74. Selva M, J. Org. Chem. 2005 70 2476
75. Davis F A., Horner C J., J. Org. Chem. 1973 38 695
76. Miura S, Shimada M, Marui S, Tamura N, Nakada Y, Tozawa R, Sakamoto J, Funabashi Y, Hosono H, Patent PCT Int. Appl. WO 2007052843 2007; Chem. Abstr. 2007, 146, 501048
77. Marziano N, Gazz. Chim. Ital. 1964 94 1137; Chem. Abstr. 1965, 63, 9909
78. Miyoshi T, Asami Y, Sato M, Ishiguro M, Kitahara T, Patent PCT Int. Appl. WO 9408956 1994; Chem. Abstr. 1994, 121, 133683
79. Fukumoto S, Watanabe T, Ikeda S, Patent PCT Int. Appl. WO 2002018350 2002; Chem. Abstr. 2002, 136, 232313
80. Bonaterra M, Martin S E., Rossi R A., Tetrahedron Lett. 2006 47 3511
81. Zhuikov V V., Russ. J. Gen. Chem. 1999 69 1796
82. Matsugi M, Murata K, Gotanda K, Nambu H, Anilkumar G, Matsumoto K, Kita Y, J. Org. Chem. 2001 66 2434