Access to polysubstituted indoles or benzothiophenes via palladium-catalyzed cross-coupling of furfural tosylhydrazones with 2-iodoanilines or 2-iodothiophenols

Chemical Communications

Volumn 51, Issue 28, 2015, Pages 6126-6129

  Yin, Biaolin ^a   Zhang, Xiaoyu ^a   Zhang, Xiaoting ^a   Peng, Hui ^a   Zhou, Wen ^b   Liu, Bo ^b   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b Guangdong Provincial Academy of Chinese Medical Sciences   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; FURFURAL; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM COMPLEX; THIOPHENOL DERIVATIVE; TOLUENE; TRANSITION ELEMENT; 2-IODOBENZENAMINE; BENZOTHIOPHENE; ORGANOMETALLIC COMPOUND; PALLADIUM; PHENOL DERIVATIVE; THIOPHENE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYST; CROSS COUPLING REACTION; DECOMPOSITION; NUCLEOPHILICITY; RING OPENING; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ANILINE COMPOUNDS; CATALYSIS; HYDRAZONES; INDOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHENOLS; THIOPHENES; TOSYL COMPOUNDS;

EID: 84925652144     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc00267b     Document Type: Article

References (92)

1. M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley-Interscience, New York, 1998
2. F. Z. Dörwald, Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999
3. Metal Carbenes in Organic Synthesis, Topics in Organometallic Chemistry, ed., K. H. Dötz, Springer-Verlag, Berling, 2004, vol. 13
4. M. P. Doyle D. C. Forbes Chem. Rev. 1998 98 911
5. A. Padwa M. D. Weingarten Chem. Rev. 1996 96 223
6. T. Ye M. A. McKervey Chem. Rev. 1994 94 1091
7. L. D. Shirtcliff S. P. McClintock M. M. Haley Chem. Soc. Rev. 2008 37 343
8. R. S. Sheridan Chem. Rev. 2013 113 7179
9. C. R. Pharr L. A. Kopff B. Bennett S. A. Reid R. J. McMahon J. Am. Chem. Soc. 2012 134 6443
10. C. Röser R. Albers W. Sander Eur. J. Org. Chem. 2001 269
11. R. V. Hoffman H. Shechter J. Am. Chem. Soc. 1978 100 7934
12. R. V. Hoffman G. G. Orphanides H. Shechter J. Am. Chem. Soc. 1978 100 7927
13. R. V. Hoffman H. Shechter J. Org. Chem. 1974 39 2939
14. R. V. Hoffman H. Shechter J. Am. Chem. Soc. 1971 93 5940
15. M. J. González E. López R. Vicente Chem. Commun. 2014 50 5379
16. F. Hu Y. Xia C. Ma Y. Zhang J. Wang Org. Lett. 2014 16 4082
17. M. J. Gonzalez L. A. Lopez R. Vicente Org. Lett. 2014 16 5780
18. J. Ma H. Jiang S. Zhu Org. Lett. 2014 16 4472
19. Y. Xia S. Qu Q. Xiao Z.-X. Wang P. Qu L. Chen Z. Liu L. Tian Z. Huang Y. Zhang J. Wang J. Am. Chem. Soc. 2013 135 13502
20. J. González J. González C. Pérez-Calleja L. A. López R. Vicente Angew. Chem., Int. Ed. 2013 52 5853
21. M. Xu T.-T. Ren K.-B. Wang C.-Y. Li Adv. Synth. Catal. 2013 355 2488
22. R. Vicente J. González L. Riesgo J. González L. A. López Angew. Chem., Int. Ed. 2012 51 8063
23. J. Barluenga L. Riesgo R. Vicente L. A. López M. Tomás J. Am. Chem. Soc. 2008 130 13528
24. Y. Kato K. Miki F. Nishino K. Ohe S. Uemura Org. Lett. 2003 5 2619
25. K. Miki T. Yokoi F. Nishino Y. Kato Y. Washitake K. Ohe S. Uemura J. Org. Chem. 2004 69 1557
26. K. Miki Y. Washitake K. Ohe S. Uemura Angew. Chem., Int. Ed. 2004 43 1857
27. K. Miki F. Nishino K. Ohe S. Uemura J. Am. Chem. Soc. 2002 124 5260
28. B. H. Lipshutz Chem. Rev. 1986 86 795
29. F. W. Lichtenthaler Acc. Chem. Res. 2002 35 728
30. A. A. Rosatella S. P. Simeonov R. F. M. Frade C. A. M. Afonso Green Chem. 2011 13 754
31. P. Gallezot Chem. Soc. Rev. 2012 41 1538
32. R. J. van Putten J. C. van der Waal E. de Jong C. B. Rasrendra H. J. Heeres J. G. de Vries Chem. Rev. 2013 113 1499
33. B.-L. Yin J.-Q. Lai Z.-R. Zhang H.-F. Jiang Adv. Synth. Catal. 2011 353 1961
34. B. Yin G. Zeng C. Cai F. Ji L. Huang Z. Li H. Jiang Org. Lett. 2012 14 616
35. B. Yin C. Cai G. Zeng R. Zhang X. Li H. Jiang Org. Lett. 2012 14 1098
36. B. Yin L. Huang X. Wang J. Liu H. Jiang Adv. Synth. Catal. 2013 355 370
37. L. Huang X. Zhang J. Li K. Ding X. Li W. Zheng B. Yin Eur. J. Org. Chem. 2014 338
38. X. Zhang L. Huang H. Peng F. Ji X. Li B. Yin Tetrahedron 2014 70 5242
39. B. Yin H. Yu Z. Li W. Zhong W. Gu Synthesis 2012 3735
40. H. Yu W. Zhong T. He W. Gu B. Yin Tetrahedron Lett. 2013 54 1256
41. B.-L. Yin J.-Q. Lai L. Huang X.-Y. Zhang F.-H. Ji Synthesis 2012 2567
42. J. Barluenga M. Tomás-Gamasa F. Aznar C. Valdés Angew. Chem., Int. Ed. 2010 49 4993
43. X. Creary J. Am. Chem. Soc. 2013 135 6570
44. J.-B. Liu H. Yan G. Lu Tetrahedron Lett. 2013 54 891
45. Q. Sha Y. Wei Tetrahedron 2013 69 3829
46. Q. Ding B. Cao J. Yuan X. Liu Y. Peng Org. Biomol. Chem. 2011 9 748
47. Q. Sha Y.-Y. Wei Org. Biomol. Chem. 2013 11 5615
48. H. E. Bartrum D. C. Blakemore C. J. Moody C. J. Hayes Chem. - Eur. J. 2011 17 9586
49. A.-H. García-Muñoz M. Tomás-Gamasa M. C. Pérez-Aguilar E. Cuevas-Yañez C. Valdés Eur. J. Org. Chem. 2012 3925
50. Q. Xiao Y. Zhang J. Wang Acc. Chem. Res. 2013 46 236
51. J. Barluenga C. Valdés Angew. Chem., Int. Ed. 2011 50 7486
52. X. Zhao Y. Zhang J. Wang Chem. Commun. 2012 48 10162
53. Z. Shao H. Zhang Chem. Soc. Rev. 2012 41 560
54. Z. Liu J. Wang J. Org. Chem. 2013 78 10024
55. Y. Xia Y. Zhang J. Wang ACS Catal. 2013 3 2586
56. X. Zeng G. Cheng J. Shen X. Cui Org. Lett. 2013 15 3022
57. Q. Xiao B. Wang L. Tian Y. Yang J. Ma Y. Zhang S. Chen J. Wang Angew. Chem., Int. Ed. 2013 52 9305
58. L. Florentino F. Aznar C. Valdés Org. Lett. 2012 14 2323
59. J. Barluenga N. Quiñones M.-P. Cabal F. Aznar C. Valdés Angew. Chem., Int. Ed. 2011 50 2350
60. J. Barluenga L. Florentino F. Aznar C. Valdés Org. Lett. 2011 13 510
61. J. Barluenga M. Tomás-Gamasa F. Aznar C. Valdés Adv. Synth. Catal. 2010 352 3235
62. J. Barluenga M. Escribano F. Aznar C. Valdés Angew. Chem., Int. Ed. 2010 49 6856
63. J. Barluenga M. Tomás-Gamasa F. Aznar C. Valdés Chem. - Eur. J. 2010 16 12801
64. J. Barluenga M. Escribano P. Moriel F. Aznar C. Valdés Chem. - Eur. J. 2009 15 13291
65. Q. Xiao J. Ma Y. Yang Y. Zhang J. Wang Org. Lett. 2009 11 4732
66. J. Barluenga M. Tomás-Gamasa P. Moriel F. Aznar C. Valdés Chem. - Eur. J. 2008 14 4792
67. R. Kudirka S. K. J. Devine C. S. Adams D. L. Van Vranken Angew. Chem., Int. Ed. 2009 48 3677
68. L. Zhou F. Ye Y. Zhang J. Wang J. Am. Chem. Soc. 2010 132 13590
69. A. Khanna C. Maung K. R. Johnson T. T. Luong D. L. Van Vranken Org. Lett. 2012 14 3233
70. P.-X. Zhou J.-Y. Luo L.-B. Zhao Y.-Y. Ye Y.-M. Liang Chem. Commun. 2013 49 3254
71. P.-X. Zhou Y.-Y. Ye Y.-M. Liang Org. Lett. 2013 15 5080
72. Y.-Y. Ye P.-X. Zhou J.-Y. Luo M.-J. Zhong Y.-M. Liang Chem. Commun. 2013 49 10190
73. B. Yin X. Zhang J. Liu X. Li H. Jiang Chem. Commun. 2014 50 8113
74. Y. Shi P. Brenner S. Bertsch K. Radacki R. D. Dewhurst Organometallics 2012 31 5599
75. R. D. Dewhurst R. Muller M. Kaupp K. Radacki K. Götz Organometallics 2010 29 4431
76. V. T. Abaev A. T. Plieva P. N. Chalikidi M. G. Uchuskin I. V. Trushkov A. V. Butin Org. Lett. 2014 16 4150
77. M. G. Uchuskin N. V. Molodtsova S. A. Lysenko V. N. Strel'nikov I. V. Trushkov A. V. Butin Eur. J. Org. Chem. 2014 2508
78. A. Kuznetsov A. Makarov A. E. Rubtsov A. V. Butin V. Gevorgyan J. Org. Chem. 2013 78 12144
79. M. G. Uchuskin N. V. Molodtsova V. T. Abaev I. V. Trushkov A. V. Butin Tetrahedron 2012 68 4252
80. A. V. Butin S. K. Smirnov F. A. Tsiunchik M. G. Uchuskin I. V. Trushkov Synthesis 2008 2943
81. A. V. Butin S. K. Smirnov I. V. Trushkov Tetrahedron Lett. 2008 49 20
82. R. C. Larock E. K. Yum J. Am. Chem. Soc. 1991 113 6689
83. K. Takanishi H. Urabe I. Kuwajima Tetrahedron Lett. 1987 28 2281
84. K. Isao H. Showay T. Toshihiko S. Makoto Tetrahedron Lett. 1980 21 3209
85. A. Saito A. Kanno Y. Hanzawa Angew. Chem., Int. Ed. 2007 46 3931
86. F. Inagaki M. Mizutani N. Kuroda C. Mukai J. Org. Chem. 2009 74 6402
87. C. Mukai Y. Takahashi Org. Lett. 2005 7 5793
88. Handbook of Thiophene-Based Materials, ed., I. F. Perepichka, and, D. F. Perepichka, Wiley-VCH Verlag, New York, 2009
89. D. A. Horton G. T. Bourne M. L. Smythe Chem. Rev. 2003 103 893
90. T. Y. Zhang J. O'Toole C. S. Proctor Sulfur Rep. 1999 22 1
91. B. Godoi R. F. Schumacher G. Zeni Chem. Rev. 2011 111 2937
92. T. W. Lyons M. S. Sanford Chem. Rev. 2010 110 1147