Divergent palladium iodide catalyzed multicomponent carbonylative approaches to functionalized isoindolinone and isobenzofuranimine derivatives

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3506-3518

  Mancuso, Raffaella ^a   Ziccarelli, Ida ^a   Armentano, Donatella ^a   Marino, Nadia ^a   Giofrè, Salvatore V ^b   Gabriele, Bartolo ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

^b Dipartimento di Scienze Del Farmaco e Dei Prodotti per la Salute   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CATALYSIS; DEHYDRATION; NUCLEOPHILES; X RAY CRYSTALLOGRAPHY;

ALKOXYCARBONYLATION; DEHYDRATING AGENTS; INTERMEDIATE FORMATION; INTRAMOLECULAR NUCLEOPHILIC ATTACK; OXIDATIVE CARBONYLATION; REACTION CONDITIONS; SUBSTRATE HYDROLYSIS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CARBONYLATION;

ALCOHOL; BENZAMIDE; BENZAMIDE DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; IODIDE; METAL; METHANOL; NITROGEN; NUCLEOPHILE; OXYGEN; PALLADIUM;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL BOND; CYCLIZATION; HYDROLYSIS; NUCLEOPHILICITY; OXIDATION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZOFURANS; CATALYSIS; IMINES; INDOLES; IODIDES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM;

EID: 84898930435     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500281h     Document Type: Article

References (122)

1. Yu, C.; Wang, T.; Xu, K.; Zhao, J.; Li, M.; Weng, S.; Zhang, J. Dyes Pigm. 2013, 96, 38-44
2. Bhardwaj, A.; Kaur, J.; Sharma, S. K.; Huang, Z.; Knaus, E. E.; Wuest, F. Bioorg. Med. Chem. Lett. 2013, 23, 163-168
3. Kar, C.; Das, G.; Adhikari, M. D.; Ramesh, A. Inorg. Chem. 2013, 52, 743-752
4. Banerjee, A.; Sahana, A.; Lohar, S.; Das, D.; Hauli, I.; Mukhopadhyay, S. K.; Safin, D. A.; Babashkina, M. G.; Garcia, Y.; Bolte, M. Chem. Commun. 2013, 49, 2527-2593
5. Pathak, S.; Debnath, K.; Hossain, S. T.; Mukherjee, S. K.; Pramanik, A. Tetrahedron Lett. 2013, 54, 3137-3143
6. Zhang, L.; Chen, X.; Zhu, Q.; Leng, Y.; Luo, X.; Jiang, H.; Liu, H.; Liu, J. Eur. J. Med. Chem. 2012, 58, 624-639
7. MacSari, I.; Besidski, Y.; Csjernyk, G.; Nilsson, L. I.; Sandberg, L.; Yngve, U.; Ahlin, K.; Bueters, T.; Lund, P.-E.; Venyike, E.; Oerther, S.; Hygge Blakeman, K.; Luo, L.; Eriksson, A. B.; Arvidsson, P. I. J. Med. Chem. 2012, 55, 6866-6880
8. Dobrokov, G. M.; Tzvetkova, P.; Chimov, A.; Dimitrov, V.; Valcheva, V.; Stoilova-Disheva, M.; Momekov, G. Eur. J. Med. Chem. 2012, 48, 45-56
9. Nagarajan, S.; Pae, A.; Nim, S.; Dimitrios, A.; Kozielski, F. J. Med. Chem. 2012, 55, 2561-2573
10. Yoo, K.-D.; Park, E.-S.; Lim, Y.; Kang, S.-I.; Yoo, S.-H.; Won, H.-H.; Kim, Y.-H.; Yoo, I.-D.; Yoo, H.-S.; Hing, J. T.; Yun, Y.-P. J. Pharmacol. Sci. 2012, 118, 171-177
11. Hardcastle, I. R.; Valeur, E.; Watson, A.; Blackburn, T. J.; Clegg, W.; Golding, B. T.; Griffin, R. J.; Haggerty, K.; Harrington, R. W.; Kemp, S.; Payne, S. L.; Revill, C. H.; Liu, J.; Ahmed, S. U.; Bennaceur, K.; Drummond, C.; Hutton, C.; Lu, X.; Newell, D. R.; Xu, Q.; Lunec, J.; Endicott, J. A.; Gruber, J.; McDonnell, J. M.; Noble, M. E. M.; Riedinger, C. J. Med. Chem. 2011, 54, 1233-1243
12. Pietra-Ottlik, M.; Potaczek, P.; Mlochowski, J.; Piasecki, E. Molecules 2010, 15, 8214-8228
13. Cai, S.-L.; Chan, Y.; Li, H.; Chen, Y.; Sun, W.-X.; Yuan, S.-S. Bioorg. Med. Chem. Lett. 2010, 20, 5649-5652
14. Temperini, C.; Cecchi, A.; Scozzafava, A.; Supuran, C. T. J. Med. Chem. 2009, 52, 322-328
15. Castro-Castillo, V.; Suarez-Rozas, C.; Pabon, A.; Blair, S.; Perez, E. G.; Cassels, B. K. Bioorg. Med. Chem. Lett. 2013, 23, 327-329
16. Nishimura, T.; Noishiki, A.; Ebe, Y.; Hayashi, T. Angew. Chem., Int. Ed. 2013, 125, 1821-1824
17. Tyagi, V.; Khan, S.; Chauhan, P. M. S. Tetrahedron Lett. 2013, 54, 1279-1284
18. Albert, J.; Granell, J.; Martinez, M.; Ortega, L.; Ariza, X.; Garcia, J.; Lamela, A.; Lopez, B.; Rodriguez, A.; Santos, D.; Calvet, T.; Font-Bardia, M. Organometallics 2013, 32, 649-659
19. Jeffrey, J. L.; Bartlett, E. S.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 2194-2197
20. Xu, K.; Zhang, S.; Hu, Y.; Zha, Z.; Wang, Z. Chem. - Eur. J. 2013, 19, 3573-3578
21. Nishimura, T.; Noishiki, A.; Ebe, Y.; Hayashi, T. Angew. Chem., Int. Ed. 2013, 52, 1777-1780
22. Zhang, L.; Zhao, F.; Zheng, M.; Zhai, Y.; Liu, H. Chem. Commun. 2013, 49, 2894-2896
23. Li, Z.; Song, L.; Li, C. J. Am. Chem. Soc. 2013, 135, 4640-4643
24. Pharikronburee, V.; Punirun, T.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Org. Biomol. Chem. 2013, 11, 2022-2033
25. Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364-5367
26. Wang, Q.; Li, C.; Zou, Y.; Wang, H.; Yi, T.; Huang, C. Org. Biomol. Chem. 2012, 10, 6740-6746
27. Shi, L.; Hu, L.; Wang, J.; Cao, X.; Gu, H. Org. Lett. 2012, 14, 1876-1879
28. Chen, M.-W.; Chen, Q.-A.; Duan, Y.; Ye, Z.-S.; Zhou, Y.-G. Chem. Commun. 2012, 48, 1698-1700
29. Zhu, C.; Falck, J. R. Tetrahedron 2012, 68, 9192-9199
30. Petronzi, C.; Palombi, L.; Intintoli, V.; Massa, A.; Collarile, S.; Filosa, R.; De Caprariis, P.; Peduto, A.; Di Mola, A.; Croce, G. Eur. J. Org. Chem. 2012, 5357-5365
31. Hesp, K. D.; Ellman, J. A.; Bergman, R. G. Org. Lett. 2012, 14, 2304-2307
32. Hrebabecky, H.; Dejmek, M.; Dracinsky, M.; Sala, M.; Nencka, R.; Leyssen, P.; Neyts, J.; Kaniakova, M.; Krsek, J. Tetrahedron 2012, 68, 1286-1298
33. Yang, G.; Zhang, W. Org. Lett. 2012, 14, 268-271
34. Zhang, H.; Leng, Y.; Liu, W.; Duan, W. Synth. Commun. 2012, 42, 1115-1127
35. Sharma, S.; Park, E.; Park, J.; Kim, I. S. Org. Lett. 2012, 14, 906-909
36. Lu, N.; Wang, L.; Li, Z.; Zhang, W. Beilstein J. Org. Chem. 2012, 8, 192-200
37. Kumar, V.; Sharma, U.; Verma, P. K.; Kumar, N.; Singh, B. Adv. Synth. Catal. 2012, 354, 870-878
38. Ordonez, M.; Tibhe, G. D.; Zamudio-Medina, A.; Viveros-Ceballos, J. L. Synthesis 2012, 44, 569-574
39. Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763-2766
40. Fujioka, M.; Morimoto, T.; Tsumagari, T.; Tanimoto, H.; Nishiyama, Y.; Kakiuchi, K. J. Org. Chem. 2012, 77, 2911-2923
41. Ju, J.; Qi, C.; Zheng, L.; Hua, R. Tetrahedron Lett. 2013, 54, 5159-5161
42. Zhang, L.; Zhang, Y.; Wang, X.; Shen, J. Molecules 2013, 18, 654-665
43. Li, L.; Wang, M.; Zhang, X.; Jiang, Y.; Ma, D. Org. Lett. 2009, 11, 1309-1312
44. Hellal, M.; Cuny, G. D. Tetrahedron Lett. 2011, 52, 5508-5511
45. Sarkar, S.; Dutta, S.; Dey, R.; Naskar, S. Tetrahedron Lett. 2012, 53, 6789-6792
46. Zhou, B.; Hou, W.; Yang, Y.; Li, Y. Chem. - Eur. J. 2013, 19, 4701-4706
47. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 123, 1096-1099
48. Ano, Y.; Chatani, N.; Tobisu, M. Org. Lett. 2012, 14, 354-357
49. Yang, G.; Zhang, W. Org. Lett. 2012, 14, 268-271
50. Chen, M.-W.; Chen, Q.-A.; Duan, Y.; Ye, Z.-S.; Zhou, Y.-G. Chem. Commun. 2012, 48, 1698-1700
51. Bubar, A.; Estey, P.; Lawson, M.; Eisler, S. J. Org. Chem. 2012, 77, 1572-1578
52. Yao, B.; Jaccoud, C.; Wang, Q.; Zhu, J. Chem. - Eur. J. 2012, 18, 5864-5868
53. Baglai, I.; Maraval, V.; Duhayon, C.; Chauvin, R.; Voitenko, Z. V.; Volovenko, Y. M. Tetrahedron 2012, 68, 6908-6913
54. Hatoum, F.; Engler, J.; Zelmer, C.; Wissen, J.; Oelgemoeller, M.; Motti, C. A.; Lex, J. Tetrahedron Lett. 2012, 53, 5573-5577
55. Reyes-Gonzalez, M. A.; Zamudio-Medina, A.; Ordonez, M. Tetrahedron Lett. 2012, 53, 5756-5758
56. Kise, N.; Isemoto, S.; Sakurai, T. Tetrahedron 2012, 68, 8805-8816
57. Sagadevan, A.; Hwang, K. C. Adv. Synth. Catal. 2012, 354, 3421-3427
58. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064-1067
59. Liu, X.; Hii, K. K. Eur. J. Org. Chem. 2012, 5181-5189
60. Wang, C.; Sun, C.; Weng, F.; Gao, M.; Liu, B.; Xu, B. Tetrahedron Lett. 2011, 52, 2984-2989
61. Yan, Z.-Y.; Tan, C.-M.; Wang, X.; Li, F.; Chen, X.-M.; Wu, W.-S.; Wang, J.-J.; Gao, G.-L. Synlett 2011, 1863-1870
62. Lu, J.; Fu, H.; Jin, Y.; Liu, H.; Jiang, Y. Org. Lett. 2011, 13, 3694-3697
63. Abdou, W. M.; Khidre, R. E.; Barghash, R. F. Synth. Commun. 2012, 42, 1967-1978
64. Del Olmo, E.; Brboza, B.; Lopez-Perez, J. L.; San Feliciano, A.; Chiaradia, L. D.; Moreno, A.; Benito, A.; Carrero-Lerida, J.; Gonzalez-Pacanowska, D.; Ruiz-Perez, L. M.; Minoz, V.; Gimenez, A.; Martinez, A. Eur. J. Med. Chem. 2011, 46, 5379-5386
65. Zhu, X.; Greig, N. H.; Yu, Q.-s.; Utsuki, T.; Holloway, H. W.; Lahiri, D. K.; Brossi, A. Heterocycles 2004, 64, 93-100
66. Del Olmo, E.; Armas, M. G.; Lopez-Perez, J. L.; Munoz, V.; Deharo, E.; Feliciano, A. S. Bioorg. Med. Chem. Lett. 2001, 11, 2123-2126
67. Cid, H. M. B.; Traenkle, C.; Baumann, K.; Pick, R.; Mies-Klomfass, E.; Kostenis, E.; Mohr, K.; Hozgrabe, U. J. Med. Chem. 2000, 43, 2155-2146
68. Kato, Y.; Takemoto, M.; Achiwa, K. Chem. Pharm. Bull. 1999, 47, 529-535
69. Gabriele, B.; Mancuso, R.; Ziccarelli, I.; Salerno, G. Tetrahedron Lett. 2012, 53, 6694-6696
70. Murata, T.; Yoneta, Y.; Mihara, J.; Domon, K.; Hatazawa, M.; Araki, K.; Shimojo, E.; Shibuya, K.; Ichihara, T.; Görgens, U.; Voerste, A.; Becker, A.; Franken, E.-M.; Müller, K.-H. (Bayer Cropscience AG) World Pat. WO2009112275A1, 2009.
71. Carta, A.; Sanna, P.; Bacchi, A. Heterocycles 2002, 57, 1079-1090
72. Bert, K.; Noel, T.; Kimpe, W.; Goeman, J. L.; Van Der Eycken, J. Org. Biomol. Chem. 2012, 10, 8539-8550
73. Mangas-Sanchez, J.; Busto, E.; Gotor-Fernandez, V.; Gotor, V. Org. Lett. 2012, 14, 1444-1447
74. Kobayashi, K.; Matsumoto, K.; Konishi, H. Heterocycles 2011, 83, 99-106
75. Allan, K. M.; Gilmore, C. D.; Stoltz, B. M. Angew. Chem., Int. Ed. 2011, 50, 4488-4491
76. Perillo, M.; Massa, A.; More, V.; Dimola, A.; Decaprariis, P.; Filosa, R.; Peduto, A. Synthesis 2011, 3027-3031
77. Kobayashi, K.; Fujita, S.; Nakai, D.; Fukumoto, S.; Fukamachi, S.; Konishi, H. Helv. Chim. Acta 2010, 93, 1274-1280
78. Angelin, M.; Rahm, M.; Fischer, A.; Brinck, T.; Ramstroem, O. J. Org. Chem. 2010, 75, 5882-5887
79. Lygin, A. V.; De Meijere, A. J. Org. Chem. 2009, 74, 4554-4559
80. Angelin, M.; Vongvilai, P.; Fischer, A.; Ramstroem, O. Chem. Commun. 2008, 768-770
81. Yoshida, H.; Fukushima, H.; Morishita, T.; Ohshita, J.; Kunai, A. Tetrahedron 2007, 63, 4793-4805
82. Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zhang, X. P. Chem. Commun. 2007, 4644-4646
83. Mehta, S.; Waldo, J. P.; Larock, R. C.; Neuenswander, B.; Lushington, G. H. ACS Comb. Sci. 2013, 15, 247-254
84. Yao, B.; Jaccoud, C.; Wang, Q.; Zhu, J. Chem. - Eur. J. 2012, 18, 5864-5868
85. Fei, X.-D.; Ge, Z.-Y.; Tang, T.; Zhu, Y.-M.; Ji, S.-J. J. Org. Chem. 2012, 77, 10321-10328
86. Schlemmer, C.; Andernach, L.; Schollmeyer, D.; Opatz, T.; Straub, B. F. J. Org. Chem. 2012, 77, 10118-10124
87. Mehta, S.; Yao, T.; Larock, R. C. J. Org. Chem. 2012, 77, 10938-10944
88. Yan, Z.-Y.; Tan, C.-M.; Wang, X.; Li, F.; Chen, X.-M.; Wu, W.-S.; Wang, J.-J.; Gao, G.-L. Synlett 2011, 1863-1870
89. Chen, D.; Jia, A.; Song, G.; Li, X. J. Org. Chem. 2011, 76, 8488-8494
90. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1-35
91. Wu, X.-F.; Neumann, H.; Beller, M. ChemSusChem 2013, 6, 229-241
92. Gabriele, B.; Mancuso, R.; Salerno, G. Eur. J. Org. Chem. 2012, 6825-6839
93. Liu, Q.; Zhang, H.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 10788-10799
94. Liu, J.; Chen, J.; Sun, W.; Xia, C. Chin. J. Catal. 2010, 31, 1-11
95. Brennfuehrer, A.; Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28-41
96. Brennfuehrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133
97. Barnard, C. F. J. Organometallics 2008, 27, 5402-5422
98. Vasapollo, G.; Mele, G. Curr. Org. Chem. 2006, 10, 1397-1421
99. Gabriele, B.; Salerno, G.; Costa, M. Top. Organomet. Chem. 2006, 18, 239-272
100. These conditions (16 atm of CO together with 6 total atm of air, considering that the autoclave was loaded under 1 atm of air) corresponded to 73.0% of CO in air and were outside the explosion limits for CO in air (ca. 16-70% at 18-20 °C at atmospheric pressure, 14.8-71.4% at 100 °C and atmospheric pressure. At higher total pressure, the range of flammability decreases; for example, at 20 atm and 20 °C the limits are ca. 19 and 60%). See: Bartish, C. M.; Drissel, G. M. In Kirk-Othmer Encyclopedia of Chemical Technology, 3 rd ed.; Grayson, M.; Eckroth, D.; Bushey, G. J.; Campbell, L.; Klingsberg, A.; van Nes, L., Eds.; Wiley-Interscience: New York, 1978; Vol 4; p 775 0.
101. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M. J. Organomet. Chem. 2001, 622, 84-88
102. Gabriele, B.; Salerno, G.; Plastina, P.; Costa, M.; Crispini, A. Adv. Synth. Catal. 2004, 346, 351-358
103. Gabriele, B.; Plastina, P.; Salerno, G.; Mancuso, R.; Costa, M. Org. Lett. 2007, 9, 3319-3322
104. Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1994, 83-87
105. Gabriele, B.; Mancuso, R.; Maltese, V.; Veltri, L.; Salerno, G. J. Org. Chem. 2012, 77, 8657-8668
106. Gabriele, B.; Veltri, L.; Mancuso, R.; Salerno, G.; Costa, M. Eur. J. Org. Chem. 2012, 2549-2559
107. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914-2921
108. de Vaal, P.; Dedieu, A. J. Organomet. Chem. 1994, 478, 121-129
109. Dyker, G.; Kellner, A. Tetrahedron Lett. 1994, 35, 7633-7636
110. Gibbs, R. A.; Krishnan, U.; Dolence, J. M.; Poulter, C. D. J. Org. Chem. 1995, 60, 7821-7829
111. Ji, J.; Wang, Z.; Lu, X. Organometallics 1996, 15, 2821-2828
112. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem. 1999, 3305-3313
113. Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 4607-4613
114. Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry; Oxford University Press: Oxford, 2001; p 345.
115. Varela-Fernandez, A.; Varela, J. A.; Saà, C. Adv. Synth. Catal. 2011, 353, 1933-1937
116. Kundu, N. G.; Khan, M. W. Tetrahedron 2000, 56, 4777-4792
117. Schultz, A. G.; Guzzo, P. R.; Nowak, D. N. J. Org. Chem. 1995, 60, 8044-8050
118. Arcadi, A.; Bianchi, G.; Marinelli, F.; Rossi, L.; Chiarini, M. Adv. Synth. Catal. 2010, 352, 136-142
119. Larock, R. C.; Mehta, S.; Waldo, J. P. J. Org. Chem. 2009, 74, 1141-1147
120. Kawamukai, S. Synthesis 1999, 1145-1148
121. Manita, J.; Masafumi, U.; Okiko, M. Org. Lett. 2011, 13, 518-521
122. Yao, B.; Jaccoud, C.; Wang, Q.; Zhu, J. Chem. - Eur. J. 2012, 18, 5864-5868