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Advances in the synthesis of aromatic and heteroaromatic carboxylic acids and their esters

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Abstract

Modern approaches to the synthesis of aromatic and heteroaromatic carboxylic acids and their esters based on the latest advances in organic chemistry are compiled and systematized in this review.

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References

  1. Feng, J.-B. and Wu, X.-F., Appl. Organometal. Chem., 2015, vol. 29, p. 63.

    Article  CAS  Google Scholar 

  2. Tomás, R.A.F., Bordado, J.C.M., and Gomes, J.F.P., Chem. Rev., 2013, vol. 113, p. 7421.

    Article  CAS  Google Scholar 

  3. Tang, S., Yuan, J., Liu, C., and Lei, A., Dalton Trans., 2014, vol. 43, p. 13460.

    Article  CAS  Google Scholar 

  4. Brennführer, A., Neumann, H., and Beller, M., Angew. Chem., Int. Ed., 2009, vol. 48, p. 4114.

    Article  CAS  Google Scholar 

  5. Gadge, S.T. and Bhanage, B.M., RSC Adv., 2014, vol. 4, p. 10367.

    Article  CAS  Google Scholar 

  6. Grigg, R. and Mutton, S.-P., Tetrahedron, 2010, vol. 66, p. 5515.

    Article  CAS  Google Scholar 

  7. Barnard, C.F.J., Organometallics, 2008, vol. 27, p. 5402.

    Article  CAS  Google Scholar 

  8. Liu, Q., Zhang, H., and Lei, A., Angew. Chem. Int., Ed., 2011, vol. 50, p. 10788.

    Article  CAS  Google Scholar 

  9. Kalck, P. and Urrutigoïty, M., Inorg. Chim. Acta, 2015, vol. 431, p. 110.

    Article  CAS  Google Scholar 

  10. Beletskaya, I. and Tyurin, V., Molecules, 2010, vol. 15, p. 4792.

    Article  CAS  Google Scholar 

  11. Beller, M. and Wu, X.-F., Transition Metal Catalyzed Carbonylation Reactions: Carbonylative Activation of C-X Bonds, Springer-Verlag: Berlin Heidelberg, 2013, vol. 2, p. 13.

    Article  Google Scholar 

  12. El’man, E.R. and Korneeva, G.A., Ross. Khim. Zh., 2006, vol. 50, p. 115.

    Google Scholar 

  13. Jia, C., Kitamura, T., and Fujiwara, Y., Acc. Chem. Res., 2001, vol. 34, p. 633.

    Article  CAS  Google Scholar 

  14. Beller, M., Cornils, B., Frohning, C.D., and Kohlpaintner, C.W., J. Mol. Catal. A: Chem., 1995, vol. 104, p. 17.

    Article  CAS  Google Scholar 

  15. Lindsey, A.S. and Jeskey, H., Chem. Rev., 1957, p. 583.

    Google Scholar 

  16. Moragas, T., Correa, A., and Martin, R., Chem. Eur. J., 2014, vol. 20, p. 1.

    Article  CAS  Google Scholar 

  17. Sakakura, T., Choi, J.-C., and Yasuda, H., Chem. Rev., 2007, vol. 107, p. 2365.

    Article  CAS  Google Scholar 

  18. Lapidus, A.L. and Ping, Ya.Yu., Russ. Chem. Rev., 1981, vol. 50, p. 63. doi 10.1070/RC1981v050n01ABEH002544

    Article  Google Scholar 

  19. Braunstein, P., Matt, D., and Nobel, D., Chem. Rev., 1980, vol. 88, p. 747.

    Article  Google Scholar 

  20. Huang, K., Sun, C.-L., and Shi, Z.-J., Chem. Soc. Rev., 2011, vol. 40, p. 2435.

    Article  CAS  Google Scholar 

  21. Colquhoun, H.M. and Thompson, D.J., Carbonylation: Direct Synthesis of Carbonyl Compounds, New York: Plenum, 1991.

    Book  Google Scholar 

  22. Correa, A. and Martin, R., Angew. Chem., Int. Ed., 2009, vol. 48, p. 6201.

    Article  CAS  Google Scholar 

  23. Riduan, S.N. and Zhang, Y., Dalton Trans., 2010, vol. 39, p. 3347.

    Article  CAS  Google Scholar 

  24. Jones, J.I., Chem. Ind. (London), 1958, p. 228.

    Google Scholar 

  25. Kito, T. and Hirao, I., Bull. Chem. Soc. Jpn., 1971, vol. 44, p. 3123.

    Article  CAS  Google Scholar 

  26. Suerbaev, Kh.A., Chepaikin, E.G., Kanapieva, F.M., and Seitenova, G.Zh., Neftekhimiya, 2009, vol. 49, p. 283.

    CAS  Google Scholar 

  27. Suerbaev, Kh.A., Kanapieva, F.M., and Seitenova, G.Zh., Dokl. Akad. Nauk Resp. Tadzhikist., 2009, vol. 52, p. 778.

    Google Scholar 

  28. Suerbaev, Kh., Akhmetova, G.B., and Shalmagambetov, K.M., Russ. J. Gen. Chem., 2005, vol. 75, p. 1498. doi 10.1007/s11176-005-0454-0

    Article  CAS  Google Scholar 

  29. Suerbaev, Kh.A., Mikhnenko, O.E., Akhmetova, G.B., Shalmagambetov, K.M., and Chepaikin, E.G., Neftekhimiya, 2005, vol. 45, p. 46.

    CAS  Google Scholar 

  30. Mikhnenko, O.E., Shalmagambetov, K.M., Dzhiembaev, B.Zh., and Suerbaev, Kh.A., Vestn. Kazakh. Nats. Univer., Ser. Khim., 2004, p. 287.

    Google Scholar 

  31. Suerbaev, Kh.A., Aldabergenov, M.K., and Kudaibergenov, N.Zh., Green Proc. Synth., 2015, vol. 4, p. 91.

    CAS  Google Scholar 

  32. Suerbaev, Kh.A., Shalmagambetov, K.M., Seitenova, G.Zh., and Kanapieva, F.M., Vestn. Kazakh. Nats. Univer., Ser. Khim., 2012, vol. 1, p. 389.

    Article  Google Scholar 

  33. Shalmagambetov, K.M. and Suerbaev, Kh.A., Khim. Tekhnol., 2011, vol. 12, p. 598.

    CAS  Google Scholar 

  34. Akhmetova, G.B., Suerbaev, Kh.A., Shalmagambetov, K.M., and Seilkhanov, T.M., Vestn. Kazakh. Nats. Univer., Ser. Khim., 2005, p. 12.

    Google Scholar 

  35. Suerbaev, Kh.A., Mikhnenko, O.E., Akhmetova, G.B., Shalmagambetov, K.M., and Chepaikin, E.G., Neftekhimiya, 2005, vol. 45, p. 364.

    CAS  Google Scholar 

  36. Suerbaev, Kh.A., Vestn. Kazakh. Nats. Univer., Ser. Khim., 2009, vol. 3, p. 25.

    Google Scholar 

  37. Hong, X., Wang, H., Liu, B., and Xu, B., Chem. Commun., 2014, vol. 50, p. 14129.

    Article  CAS  Google Scholar 

  38. Peng, X., Zhu, Y., Ramirez, T.A., Zhao, B., and Shi, Y., Org. Lett., 2011, vol. 13, p. 5244.

    Article  CAS  Google Scholar 

  39. Pan, C., Han, J., Zhang, H., and Zhu, C., J. Org. Chem., 2014, vol. 79, p. 5374.

    Article  CAS  Google Scholar 

  40. Yu, W.Y., Sit, W.N., Lai, K.M., Zhou, Z., and Chan, A.S., J. Am. Chem. Soc., 2008, vol. 130, p. 3304.

    Article  CAS  Google Scholar 

  41. Huang, Y., Li, G., Huang, J., and You, J., Org. Chem. Front., 2014, vol. 1, p. 347.

    Article  CAS  Google Scholar 

  42. Denmark, S.E. and Regens, C.S., Acc. Chem. Res., 2008, vol. 41, p. 1486.

    Article  CAS  Google Scholar 

  43. Friis, S.D., Andersen, T.L., and Skrydstrup, T., Org. Lett., 2013, vol. 15, p. 1378.

    Article  CAS  Google Scholar 

  44. Reimer, K. and Tiemann, F., Ber., 1876, vol. 9, p. 1285.

    Article  Google Scholar 

  45. Komiyama, M. and Hirai, H., J. Am. Chem. Soc., 1984, vol. 106, p. 174.

    Article  CAS  Google Scholar 

  46. Komiyama, M. and Hirai, H., Makromol. Chem., Rapid Commun., 1981, vol. 2, p. 661.

    Article  CAS  Google Scholar 

  47. Komiyama, M., Sugiura, I., and Hirai, H., J. Mol. Catal., 1986, vol. 36, p. 271.

    Article  CAS  Google Scholar 

  48. Takahashi, K., Chem. Rev., 1998, vol. 98, p. 2013.

    Article  CAS  Google Scholar 

  49. Sasson, Y. and Razintsky, M., J. Chem. Soc., Chem., 1985, p. 1134.

    Google Scholar 

  50. Hirai, H. and Mihori, H., Chem. Lett., 1992, p. 1523.

    Google Scholar 

  51. Hirai, H., Shiraishi, Y., Mihori, H., and Saito, K., Polymer. J., 1996, vol. 28, p. 91.

    Article  CAS  Google Scholar 

  52. Hirai, H., Pure Appl. Chem., 1994, vol. A31, p. 1491.

    CAS  Google Scholar 

  53. Shiraishi, Y., Kojima, S., Tomita, H., Ohsuka, H., Kawamura, T., Toshima, N., and Hirai, H., Polym. J., 1996, vol. 28, p. 619.

    Article  CAS  Google Scholar 

  54. Hirai, H., Polim. Adv. Technol., 1997, vol. 8, p. 666.

    Article  CAS  Google Scholar 

  55. Komiyama, M. and Hirai, H., J. Am. Chem. Soc., 1984, vol. 106, p. 174.

    Article  CAS  Google Scholar 

  56. Hirai, H., US Patent no. 5319134, 1994; Сhem. Abstr., 1993, vol. 119, p. 116963.

    Google Scholar 

  57. Hirai, H. and Shiraishi, Y., React. Funct. Polymer., 2007, vol. 67, p. 1115.

    Article  CAS  Google Scholar 

  58. Hirai, H., Polimer. Adv. Technol., 1997, vol. 8, p. 666.

    Article  CAS  Google Scholar 

  59. Hirai, H., Shiraishi, Y., and Saito, K., Macromol. Rapid Commun., 1995, vol. 16, p. 31.

    Article  CAS  Google Scholar 

  60. Hirai, H., Mihori, H., and Terakado, R., Macromol. Rapid Commun., 1993, vol. 14, p. 439.

    Article  CAS  Google Scholar 

  61. Shiraishi, Y., Toshima, N., Kawamura, T., Mihori, H., Shirai, H., and Hirai, H., J. Mol. Catal. A: Chem., 1999, vol. 139, p. 149.

    Article  CAS  Google Scholar 

  62. Shiraishi, Y., Tashiro, S., and Toshima, N., Chem. Lett., 2000, p. 828.

    Google Scholar 

  63. Hirai, H., Shiraishi, Y., and Shirai, H., Macromol. Rapid Commun., 1995, vol. 16, p. 697.

    Article  CAS  Google Scholar 

  64. Leebrick, J.R., US Patent no. 3297771, 1967; Chem. Abstr., 1967, vol. 66, p. 65270.

    Google Scholar 

  65. Kumai, S., US Patent no. 5241111, 1993; Chem. Abstr., 1991, vol. 115, p. 207663.

    Google Scholar 

  66. Kumai, S., JP Patent no. 04149143, 1992; Chem. Abstr., 1992, vol. 117, p. 191510.

    Google Scholar 

  67. Kumai, S., JP Patent no. 03161467, 1991; Chem. Abstr., 1991, vol. 115, p. 207663.

    Google Scholar 

  68. Kumai, S., JP Patent no. 07165638, 1995; Chem. Abstr., 1995, vol. 123, p. 339372.

    Google Scholar 

  69. Kumai, S., JP Patent no. 0449264, 1992; Chem. Abstr., 1992, vol. 117, p. 48085.

    Google Scholar 

  70. Kumai, S., JP Patent no. 03161450, 1991; Chem. Abstr., 1991, vol. 115, p. 207663.

    Google Scholar 

  71. Uemura, S., Sasaki, O., and Okano, M., Chem. Commun., 1970, p. 1139.

    Google Scholar 

  72. Khusnutdinov, R.I., Schadneva, N.A., Bayguzina, A.R., Lavrentieva, Yu.Yu., Dzhemilev, U.M., Burangulova, R.Yu., and Smirnov, A.A., Arkivoc, 2004, vol. XI, p.53.

    Google Scholar 

  73. Khusnutdinov, R.I., Shchadneva, N.A., Baiguzina, A.R., Mukminov, R.R., Mayakova, Yu.Yu., Smirnov, A.A., and Dzhemilev, U.M., Neftekhimiya, 2008, vol. 48, p. 467.

    CAS  Google Scholar 

  74. Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. Chem. Bull., 2013, vol. 62, p. 93. doi 10.1007/ s11172-013-0012-6

    Article  CAS  Google Scholar 

  75. Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. J. Org. Chem., 2011, vol. 47, p. 437. doi 10.1134/S1070428011030195

    Article  CAS  Google Scholar 

  76. Khusnutdinov, R.I., Baiguzina, A.R., Mukminov, R.R., Akhmetov, I.V., Gubaidullin, I.M., Spivak, S.I., and Dzhemilev, U.M., Russ. J. Org. Chem., 2010, vol. 46, p. 1053. doi 10.1134/S1070428010070158

    Article  CAS  Google Scholar 

  77. Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. J. Org. Chem., 2010, vol. 46, p. 1399. doi 10.1134/S1070428010090228

    Article  CAS  Google Scholar 

  78. Khusnutdinov, R.I., Bayguzina, A.R., Denisov, K.Y., and Dzhemilev, U.M., Mendeleev Commun., 2015, vol. 25, p. 219.

    Article  CAS  Google Scholar 

  79. Dzhemilev, U.M., RF Patent no. 2481324, 2013; Chem. Abstr., 2013, vol. 158, p. 636247.

    Google Scholar 

  80. Dzhemilev, U.M., Khusnutdinov, R.I., Baiguzina, A.R., and Erokhina, I.S., Zayavka na Izobret. no. 2016133805, 17.08.2016 (pol. resh. 17.10. 2016).

    Google Scholar 

  81. Baiguzina, A.R., Erokhina, I.S., and Khusnutdinov, R.I., Russ. J. Gen. Chem., 2017, vol. 87, p. 389. doi 10.1134/ S1070363217030057

    Article  CAS  Google Scholar 

  82. Dzhemilev, U.M., RF Patent no. 2536591; Chem. Abstr., 2014, vol. 162, p. 2156632.

    Google Scholar 

  83. Bayguzina, A.R., Erokhina, I.S., and Khusnutdinov, R.I., Russ. J. Org. Chem., 2017, vol. 53, p. 359. doi 10.1134/ S1070428017030071

    Article  CAS  Google Scholar 

  84. Dzhemilev, U.M., RF Patent no. 2566086, 2015; Chem. Abstr., 2015, vol. 163, p. 1675812.

    Google Scholar 

  85. Dzhemilev, U.M., RF Patent no. 2359968, 2009; Chem. Abstr., 2009, vol. 151, p. 77902.

    Google Scholar 

  86. Dzhemilev, U.M., RF Patent no. 2404176, 2010; Chem. Abstr., 2010, vol. 153, p. 618713.

    Google Scholar 

  87. Dzhemilev, U.M., RF Patent no. 2402541, 2010; Chem. Abstr., 2010, vol. 153, p. 55491.

    Google Scholar 

  88. Mukminov, R.R., Candidate Sci. (Chem.) Dissertation, Ufa, 2010.

    Google Scholar 

  89. Mukminov, R.R., Sintez karbonovykh kislot ryada tiofena, pirrola, furana i izokhinona. Sintez, struktura, primenenie (Synthesis of Carboxylic Acids of a Series of Thiophene, Pyrrole, Furan and Isoquinoline. Synthesis, Structure, Application), Saarbrucken: LAP Lambert Academic Publishing, 2011.

    Google Scholar 

  90. Gromova, G.P., Belen’kii, L.I., and Krayushkin, M.M., Chem. Heterocycl. Compd., 1993, vol. 29, p. 889. doi 10.1007/BF00534264

    Article  Google Scholar 

  91. Belen’kii, L.I., Gromova, G.P., and Krayushkin, M.M., Chem. Heterocycl. Compd., 1993, vol. 8, p. 883. doi 10.1007/BF00534263

    Article  Google Scholar 

  92. Belen’kii, L.I. and Gul’tai, V.P., Chem. Heterocycl. Compd., 1981, vol. 17, p. 523. doi 10.1007/BF00503474

    Article  Google Scholar 

  93. Khusnutdinov, R.I., Baiguzina, A.R., Mukminov, R.R., and Dzhemilev, U.M., J. Appl. Chem., 2009, vol. 82, p. 340. doi 10.1134/S1070427209020335

    CAS  Google Scholar 

  94. Dzhemilev, U.M., RF Patent no. 2404173, 2010; Chem. Abstr., 2010, vol. 153, p. 600652.

    Google Scholar 

  95. Khusnutdinov, R.I., Baiguzina, A.R., Smirmov, A.A., Mukminov, R.R., and Dzhemilev, U.M., J. Appl. Chem., 2007, vol. 80, p. 1687. doi 10.1134/S1070427207100163

    CAS  Google Scholar 

  96. Dzhemilev, U.M., RF Patent no. 2319690, 2008; Chem. Abstr., 2008, vol. 148, p. 331337.

    Google Scholar 

  97. Dzhemilev, U.M., RF Patent no. 2467004, 2012; Chem. Abstr., 2012, vol. 157, p. 708400.

    Google Scholar 

  98. Dzhemilev, U.M., RF Patent no. 2455299, 2012; Chem. Abstr., 2012, vol. 157, p. 165411.

    Google Scholar 

  99. Dzhemilev, U.M., RF Patent no. 2404162, 2010; Chem. Abstr., 2010, vol. 153, p. 600656.

    Google Scholar 

  100. Dzhemilev, U.M., RF Patent no. 2402535, 2010; Chem. Abstr., 2010, vol. 153, p. 554932.

    Google Scholar 

  101. Khusnutdinov, R.I., Baiguzina, A.R., and Mukminov, R.R., Russ. J. Org. Chem., 2010, vol. 46, p. 706. doi 10.1134/S1070428010050192

    Article  CAS  Google Scholar 

  102. Dzhemilev, U.M., RF Patent no. 2404166, 2010, Chem. Abstr., 2010, vol. 153, p. 600680.

    Google Scholar 

  103. Grushin, V.V. and Alper, H., Organometallics, 1993, vol. 12, p. 3846.

    Article  CAS  Google Scholar 

  104. Natte, K., Dumrath, A., Neumann, H., and Beller, M., Angew. Chem., Int. Ed., 2014, vol. 53, p. 10090.

    Article  CAS  Google Scholar 

  105. Corey, E.J. and Hegedus, L.S., J. Am. Chem. Soc., 1969, vol. 91, p. 1233.

    Article  CAS  Google Scholar 

  106. Georgsson, J., Hallberg, A., and Larhed, M., J. Comb. Chem., 2003, vol. 5, p. 350.

    Article  CAS  Google Scholar 

  107. Roberts, B., Liptrot, D., Alcaraz, L., Luker, T., and Stocks, M.J., Org. Lett., 2010, vol. 12, p. 4280.

    Article  CAS  Google Scholar 

  108. Kaiser, N.-F.K., Hallberg, A., and Larhed, M., J. Comb. Chem., 2002, vol. 4, p. 109.

    Article  CAS  Google Scholar 

  109. Odell, L.R., Sävmarker, J., and Larhed, M., Tetrahedron Lett., 2008, vol. 49, p. 6115.

    Article  CAS  Google Scholar 

  110. Odell, L.R., Russo, F., and Larhed, M., Synlett., 2012, vol. 23, p. 685.

    Article  CAS  Google Scholar 

  111. Lesma, G., Sacchetti, A., and Silvani, A., Synthesis, 2006, vol. 4, p. 594.

    Google Scholar 

  112. Lagerlund, O. and Larhed, M., J. Comb. Chem., 2006, vol. 8, p. 4.

    Article  CAS  Google Scholar 

  113. Baburajan, P., Senthilkumaran, R., and Elango, K.P., New J. Chem., 2013, vol. 37, p. 3050.

    Article  CAS  Google Scholar 

  114. Bowman, M.D., Holcomb, J.L., Kormos, C.M., Leadbeater, N.E., and Williams, V.A., Org. Proc. Res. Dev., 2008, vol. 12, p. 41.

    Article  CAS  Google Scholar 

  115. Iannelli, M., Bergamelli, F., Kormos, C.M., Paravisi, S., and Leadbeater, N.E., Org. Proc. Res. Dev., 2009, vol. 13, p. 634.

    Article  CAS  Google Scholar 

  116. Bowman, M.D., Schmink, J.R., McGowan, C.M., Kormos, C.M., and Leadbeater, N.E., Org. Proc. Res. Dev., 2008, p. 1078.

    Google Scholar 

  117. Kelly, C.B., Lee, C., Mercadante, M.A., and Leadbeater, N.E., Org. Proc. Res. Dev., 2011, vol. 15, p. 717.

    Article  CAS  Google Scholar 

  118. Mercadante, M.A. and Leadbeater, N.E., Org. Biomol. Chem., 2011, vol. 9, p. 6575.

    Article  CAS  Google Scholar 

  119. Shibahara, F., Kinoshita, S., and Nozaki, K., Org. Lett., 2004, vol. 6, p. 2437.

    Article  CAS  Google Scholar 

  120. Sakakibara, K., Yamashita, M., and Nozaki, K., Tetrahedron Lett., 2005, vol. 46, p. 959.

    Article  CAS  Google Scholar 

  121. Cacchi, S., Fabrizi, G., and Goggiamani, A., Org. Lett., 2003, vol. 5, p. 4269.

    Article  CAS  Google Scholar 

  122. Berger, P., Bessmernykh, A., Caille, J.C., and Mignonac, S., Synthesis, 2006, vol. 18, p. 3106.

    Google Scholar 

  123. Cacchi, S., Cotet, C.L., Fabrizi, G., Forte, G., Goggiamani, A., Martín, L., Martínez, S., Molins, E., Moreno-Mañas, M., Petrucci, F., Roig, A., and Vallribera, A., Tetrahedron, 2007, vol. 63, p. 2519. doi 10.1016/j.tet.2006.12.024

    Article  CAS  Google Scholar 

  124. Buu-Hoi, Ng.Ph. and Janicaud, J., Bull. Soc. Chim., 1945, vol. 12, p. 640.

    CAS  Google Scholar 

  125. Kochi, T., Urano, S., Seki, H., Mizushima, E., Sato, M., and Kakiuchi, F., J. Am. Chem. Soc., 2009, vol. 131, p. 2792.

    Article  CAS  Google Scholar 

  126. Schareina, T., Zapf, A., Cotte, A., Cotta, M., and Beller, M., Adv. Synth. Catal., 2010, vol. 352, p. 1205.

    Article  CAS  Google Scholar 

  127. Ko, S., Lee, C., Choi, M.-G., Na, Y., and Chang, S., J. Org. Chem., 2003, vol. 68, p. 1607.

    Article  CAS  Google Scholar 

  128. Carpentier, J.-F., Castanet, Y., Brocard, J., Mortreux, A., and Petit, F., Tetrahedron Lett., 1991, vol. 32, p. 4705.

    Article  CAS  Google Scholar 

  129. Carpentier, J.-F., Castanet, Y., Brocard, J., Mortreux, A., and Petit, F., Tetrahedron Lett., 1992, vol. 33, p. 2001.

    Article  CAS  Google Scholar 

  130. Carpentier, J.-F., Finet, E., Castanet, Y., Brocard, J., and Mortreux, A., Tetrahedron Lett., 1994, vol. 35, p. 4995.

    Article  CAS  Google Scholar 

  131. Carpentier, J.-F., Castanet, Y., Mortreux, A., and Petit, F., J. Organometal. Chem., 1994, vol. 482, p. 31.

    Article  CAS  Google Scholar 

  132. Shang, R., Fu, Y., Li, J., Zhang, S., Guo, Q., and Liu, L., J. Am. Chem. Soc., 2009, vol. 131, p. 5738.

    Article  CAS  Google Scholar 

  133. Carpentier, J.F., Petit, F., Mortreux, A., Dufaud, V., Basset, J.M., and Thivolle-Cazat, J., J. Mol. Catal., 1993, vol. 81, p. 1.

    Article  CAS  Google Scholar 

  134. Jenner, G. and Taleb, A.B., J. Organometal. Chem., 1994, vol. 470, p. 257.

    Article  CAS  Google Scholar 

  135. Jenner, G., Appl. Catal., A: General, 1995, vol. 121, p. 25.

    Article  CAS  Google Scholar 

  136. Ueda, T., Konishi, H., and Manabe, K., Org. Lett., 2012, vol. 14, p. 3100.

    Article  CAS  Google Scholar 

  137. Fujihara, T., Hosoki, T., Katafuchi, Y., Iwai, T., Terao, J., and Tsuji, Y., Chem. Commun., 2012, vol. 48, p. 8012.

    Article  CAS  Google Scholar 

  138. Li, H., Neumann, H., Beller, M., and Wu, X.F., Angew. Chem., 2014, vol. 126, p. 3247.

    Article  Google Scholar 

  139. Chen, G., Leng, Y., Yang, F., Wang, S., and Wu, Y., Chin. J. Chem., 2013, vol. 31, p. 1488.

    Article  CAS  Google Scholar 

  140. Wu, J., Lan, J., Guo, S., and You, J., Org. Lett., 2014, vol. 16, p. 5862.

    Article  CAS  Google Scholar 

  141. Alonso, N., de M. Munoz, J., Egle, B., Vrijdag, J.L., De Borggraeve, W.M., de la Hoz, A., Díaz-Ortiz, A., and Alcázar, J., J. Flow. Chem., 2014, vol. 4, p. 105. doi 10.1556/JFC-D-14-00005

    Article  CAS  Google Scholar 

  142. Ueda, T., Konishi, H., and Manabe, K., Org. Lett., 2012, vol. 14, p. 5370.

    Article  CAS  Google Scholar 

  143. Kondo, T., Tantayanon, S., Tsuji, Y., and Watanabe, Y., Tetrahedron Lett., 1989, vol. 30, p. 4137.

    Article  CAS  Google Scholar 

  144. Jenner, G., Nahmed, E.M., and Leismann, H., J. Organometal. Chem., 1990, vol. 387, p. 315.

    Article  CAS  Google Scholar 

  145. Park, J., Han, S.H., Sharma, S., Han, S., Shin, Y., Mishra, N.K., Kwak, J.H., Lee, C.H., Lee, J., and Kim, I.S., J. Org. Chem., 2014, vol. 79, p. 4735.

    Article  CAS  Google Scholar 

  146. Khatun, N., Banerjee, A., Santra, S.K., Ali, W., and Patel, B.K., RSC Adv., 2015, vol. 5, p. 36461.

    Article  CAS  Google Scholar 

  147. Rout, S.K., Guin, S., Gogoi, A., Majji, G., and Patel, B.K., Org. Lett., 2014, vol. 16, p. 1614.

    Article  CAS  Google Scholar 

  148. Mondal, B., Sahoo, S.C., and Pan, S.C., Eur. J. Org. Chem., 2015, vol. 14, p. 3135.

    Article  CAS  Google Scholar 

  149. Behera, A., Rout, S.K., Guin, S., and Patel, B.K., RSC Adv., 2014, vol. 4, p. 55115.

    Article  CAS  Google Scholar 

  150. Khemnar, A.B. and Bhanage, B.M., Org. Biomol. Chem., 2014, vol. 12, p. 9631.

    Article  CAS  Google Scholar 

  151. Rout, S.K., Guin, S., Ghara, K.K., Banerjee, A., and Patel, B.K., Org. Lett., 2012, vol. 14, p. 3982.

    Article  CAS  Google Scholar 

  152. Majji, G., Guin, S., Gogoi, A., Rout, S.K., and Patel, B.K., Chem. Commun., 2013, vol. 49, p. 3031.

    Article  CAS  Google Scholar 

  153. Wang, S., Yang, Z., Liu, J., Xie, K., Wang, A., Chen, X., and Tan, Z., Chem. Commun., 2012, vol. 48, p. 9924.

    Article  CAS  Google Scholar 

  154. Zhou, W., Li, P., Zhang, Y., and Wang, L., Adv. Synth. Catal., 2013, vol. 355, p. 2343.

    Article  CAS  Google Scholar 

  155. Zheng, R., Zhou, Q., Gu, H., Jiang, H., Wu, J., Jin, Z., and Chen, R., Tetrahedron Lett., 2014, vol. 55, p. 5671.

    Article  CAS  Google Scholar 

  156. Yang, D., Yang, H., and Fu, H., Chem. Commun., 2011, vol. 47, p. 2348.

    Article  CAS  Google Scholar 

  157. Rueggeberg, W.H.C., Frantz, R.K., and Ginsburg, A., Ind. Eng. Chem., 1946, vol. 38, p. 624.

    Article  CAS  Google Scholar 

  158. Walter, H.C.R., US Patent no. 2552591, 1951; Chem. Abstr., 1951, vol. 45, p. 55782.

    Google Scholar 

  159. Flack, N.J., US Patent no. 1542264, 1925; Chem. Abstr., 1925, vol. 19, p. 18075.

    Google Scholar 

  160. Ayrey, G. and Moor, C.G., J. Chem. Soc., 1956, p. 1356.

    Google Scholar 

  161. Villani, A.J., Elzkorn, F., Roter, G.A., and Heys, J.R., J. Labelled Comp. Radiopharm., 1988, vol. 25, p. 1339.

    Article  CAS  Google Scholar 

  162. Gross, H., Rusche, J., and Mirsch, M., Chem. Ber., 1963, vol. 96, p. 1382.

    Article  CAS  Google Scholar 

  163. Ueda, T., Konishi, H., and Manabe, K., Angew. Chem., Int. Ed., 2013, vol. 52, p. 8611.

    Article  CAS  Google Scholar 

  164. Menegheli, P., Rezende, M.C., and Zucco, C., Synth. Commun., 1987, vol. 17, p. 457.

    Article  CAS  Google Scholar 

  165. Hasan, I., Marinelli, E.R., Lin, L.-C.C., Fowler, F.W., and Levy, A.B., J. Org. Chem., 1981, vol. 46, p. 157.

    Article  CAS  Google Scholar 

  166. Donohoe, T.J., Headley, C.E., Cousins, R.P.C., and Cowley, A., Org. Lett., 2003, vol. 5, p. 999.

    Article  CAS  Google Scholar 

  167. Harbuck, J.W. and Rapoport, H., J. Org. Chem., 1972, vol. 37, p. 3618.

    Article  CAS  Google Scholar 

  168. Sonnet, P.E., J. Med. Chem., 1972, vol. 15, p. 97.

    Article  CAS  Google Scholar 

  169. Mackie, R.K., Mhatre, S., and Tedder, J.M., J. Fluor. Chem., 1977, vol. 10, p. 437.

    Article  CAS  Google Scholar 

  170. Pramanik, S., Reddy, R.R., and Ghorai, P., Org. Lett., 2015, vol. 17, p. 1393.

    Article  CAS  Google Scholar 

  171. Glueck, S.M., Gumus, S., Fabian, W.M.F., and Faber, K., Chem. Soc. Rev., 2010, vol. 39, p. 313.

    Article  CAS  Google Scholar 

  172. Fesko, K. and Gruber-Khadjaw, M., ChemCatChem., 2013, vol. 5, p. 1248.

    Article  CAS  Google Scholar 

  173. Erb, T.J., Appl. Environ. Microbiol., 2011, vol. 77, p. 8466.

    Article  CAS  Google Scholar 

  174. Kourist, R., Guterl, J.-K., Miyamoto, K., and Sieber, V., ChemCatChem., 2014, vol. 6, p. 689.

    Article  CAS  Google Scholar 

  175. Von Borzyskowski, L.S., Rosenthal, R.G., and Erb, T.J., J. Biotechnol., 2013, vol. 168, p. 243.

    Article  CAS  Google Scholar 

  176. Aresta, M. and Dibenedetto, A., Reaction Mechanisms in Carbon Dioxide Conversion, Berlin–Heidelberg: Springer-Verlag, 2016, vol. 7, p. 347.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Russia

    R. I. Khusnutdinov, A. R. Baiguzina & U. M. Dzhemilev

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  1. R. I. Khusnutdinov
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  2. A. R. Baiguzina
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  3. U. M. Dzhemilev
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Original Russian Text © R.I. Khusnutdinov, A.R. Baiguzina, U.M. Dzhemilev, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1101–1155.

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Khusnutdinov, R.I., Baiguzina, A.R. & Dzhemilev, U.M. Advances in the synthesis of aromatic and heteroaromatic carboxylic acids and their esters. Russ J Org Chem 53, 1113–1169 (2017). https://doi.org/10.1134/S1070428017080012

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