Item request has been placed! ×
Item request cannot be made. ×
loading  Processing Request

Direct Access to Amides from Nitro-Compounds via Aminocarbonylation and Amidation Reactions: A Minireview.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
  • المؤلفون: Barak DS;Barak DS; Batra S; Batra S; Batra S
  • المصدر:
    Chemical record (New York, N.Y.) [Chem Rec] 2021 Dec; Vol. 21 (12), pp. 4059-4087. Date of Electronic Publication: 2021 Sep 02.
  • نوع النشر :
    Journal Article; Review
  • اللغة:
    English
  • معلومة اضافية
    • المصدر:
      Publisher: Wiley Country of Publication: United States NLM ID: 101085550 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1528-0691 (Electronic) Linking ISSN: 15280691 NLM ISO Abbreviation: Chem Rec Subsets: MEDLINE
    • بيانات النشر:
      Original Publication: New York : Wiley, c2000-
    • الموضوع:
    • نبذة مختصرة :
      The ubiquity of the amide bond in functional molecules including proteins, natural products, pharmaceuticals, agrochemicals and materials provides impetus to design and develop newer strategies for the generation of this linkage. Owing to growing awareness about sustainability and development of benign strategies, the traditional route of synthesis of amides via reaction between carboxylic acids and amines in the presence of stoichiometric amount of coupling reagents is tagged to be harsh and wasteful. In one of the unconventional routes, nitro compounds are used directly as amine surrogates for preparing amides mostly via aminocarbonylation and amidation reactions. Typically, such processes involves nitroarenes owing to their propensity to transform into nitroso, hydroxylamine, diazo, hydrazine or aniline intermediates in situ under the influence of suitable catalyst or oxidant. This short review provides the comprehensive overview of these reactions including insight into the scope and their mechanisms.
      (© 2021 The Chemical Society of Japan & Wiley-VCH GmbH.)
    • References:
      G. Arthur, The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science, Wiley-Interscience, 2000.
       .
      C. A. G. N. Montalbetti, V. Falque, Tetrahedron 2005, 61, 10827-10852;.
      S. Mahesh, K.-C. Tang, M. Raj, Molecules 2018, 23, 2615.
       .
      C. Nájera, M. Yus, Natural products with polyene amide structures. in Studies in Natural Products Chemistry: Bioactive Natural Products (B) (Eds: A. Rahman), Science Direct Book Series 2000, 373-455;.
      Z. Jin, Nat. Prod. Rep. 2009, 26, 363-381;.
      Q. A. Ngo, T. Y. Tran, T. H. Nguyen, V. T. Nguyen, H. A. Duong, H. V. Pham, Nat. Prod. Res. 2021, 35, 1384-1387.
       .
      J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347;.
      S. D. Roughley, A. M. Jordan, J. Med. Chem. 2011, 54, 3451-3479;.
      H. Lundberg, F. Tinnis, N. Selander, H. Adolfsson, Chem. Soc. Rev. 2014, 43, 2714-2742.
       .
      M. M. Joullié, K. M. Lassen, Arkivoc 2010, 8, 189-250;.
      E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606-631;.
      H. Lundberg, F. Tinnis, N. Selander, H. Adolfsson, Chem. Soc. Rev. 2014, 43, 2714-2742;.
      A. P. Zarecki, J. L. Kolanowski, W. T. Markiewicz, Molecules 2020, 25, 1761.
       .
      A. El-Faham, F. Albericio, Chem. Rev. 2011, 111, 6557-6602;.
      J. R. Dunetz, J. M. Javier Magano, G. Weisenburger, Org. Process Res. Dev. 2016, 20, 140-177;.
      K. J. McKnelly, W. Sokol, J. S. Nowick, J. Org. Chem. 2020, 85, 1764-1768.
      D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey, J. L. Leazer, Jr., R. J. Linderman, K. Lorenz, J. Manley, B. A. Pearlman, A. Wells, A. Zaksh, T. Y. Zhang Green Chem. 2007, 9, 411-420.
       .
      C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405-3415;.
      S. Roy, S. Roy, G. W. Gribble, Tetrahedron 2012, 68, 9867-9923;.
      R. M. Lanigan, T. D. Sheppard, Eur. J. Org. Chem. 2013, 7453-7465;.
      X. Wang, Nat. Catal. 2019, 2, 98-102.
       .
      V. R. Pattabiraman, J. W. Bode, Nature 2011, 480, 471-479;.
      R. M. de Figueiredo, J. S. Suppo, J. M. Campagne, Chem. Rev. 2016, 116, 12029-12122;.
      M. T. Sabatini, V. Karaluka, R. M. Lanigan, L. T. Boulton, M. Badland, T. D. Sheppard, Chem. Eur. J. 2018, 24, 7033-7043;.
      M. T. Sabatini, L. T. Boulton, H. F. Sneddon, T. D. Sheppard, Nat. Catal. 2019, 2, 10-17;.
      E. Massolo, M. Pirola, M. Benaglia, Eur. J. Org. Chem. 2020, 4641-4651.
       .
      J. F. Hartwig, S. Shekhar, Q. Shen, F. Barrios-Landeros, Synthesis of anilines in PATAI's Chemistry of Functional Groups; Ed.: Z. Rappoport, Wiley-VCH: New York, 2007, 455-536;.
      H. K. Kadam, S. G. Tilve, RSC Adv. 2015, 5, 83391-83407.
      P. T. Moshapo, S. B. Simelane, Arkivoc 2020, part v, 190-215.
      W. Reppe, H. Krcper, Liebigs Ann. Chem. 1953, 582, 38-71.
      A. Schoenberg, R. F. Heck, J. Org. Chem. 1974, 39, 3327.
       .
      I. Ojima, C. Commandeur, W.-H. Chiou, Comprehensive Organometallic Chemistry III Eds D. Mingos, P. Michael, R. H. Crabtree, 2007, 11, 511-555;.
      M. Kiss, A. Takacs, L. Kollar, Curr. Green Chem. 2015, 2, 319-338;.
      J.-B. Peng, H.-Q. Geng, X.-F. Wu, Chem 2019, 5, 526-552;.
      L.-J. Cheng, N. P. Mankad, Acc. Chem. Res. 2021, 54, 2261-2274.
      X. Fang, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 14089-14093;.
      Angew. Chem. 2013, 125, 14339-14343.
      J.-B. Peng, H.-Q. Geng, D. Li, X. Qi, J. Ying, X.-F. Wu, Org. Lett. 2018, 20, 4988-4993.
      L. Yang, L. Shi, C. Xia, F. Li, Chin. J. Catal. 2020, 41, 1152-1160.
      J.-B. Peng, H.-Q. Geng, F.-P. Wu, D. Li, X.-F. Wu, J. Catal. 2019, 375 519-523.
      T. Mise, P. Hong, Hiroshi Yamazaki Chem. Lett. 1980, 9, 439-440.
      F. Zhou, D.-S. Wang, X. Guan, T. G. Driver, Angew. Chem. Int. Ed. 2017, 56, 4530-4534;.
      Angew. Chem. 2017, 129, 4601-4605.
      C. W. Cheung, M. L. Ploeger, X. Hu, Chem. Sci. 2018, 9, 655-659.
      S. Zhao, N. P. Mankad, Org. Lett. 2019, 21, 10106-10110.
      J.-B. Peng, D. Li, H.-Q. Geng, X.-F. Wu, Org. Lett. 2019, 21, 4878-4881.
      N. Shen, C. W. Cheung, J.-A. Ma, Chem. Commun. 2019, 55, 13709-13712.
      L.-M. Yang, S.-S. Li, Y.-Y. Zhang, J.-L. Lu, J.-T. Deng, A.-J. Ma, X.-Z. Zhang, S.-Y. Zhang, J.-B. Peng, Adv. Synth. Catal. 2021, 363, 2061-2065.
      V. Thakur, A. Kumar, N. Sharma, A. K. Shil, P. Das, Adv. Synth. Catal. 2018, 360, 432-437.
      D. C. Owsley, J. J. Bloomfield, Synthesis 1977, 2, 118-119.
      T.-L. Ho, J. Org. Chem. 1977, 42, 3755.
      Y. Watanabe, Y. Tsuji, T. Kondo, R. Takeuchi, J. Org. Chem. 1984, 49, 4451-4455.
      K. Y. Lee, J. M. Kim, J. N. Kim, Bull. Korean Chem. Soc. 2002, 23, 1359-1360.
      X. Du, M. Zheng, S. Chen, Z. Xu, Synlett 2006, 12, 1953-1955.
      V. Kumar, M. Kumar, S. Sharma, N. Kumar, RSC Adv. 2014, 4, 11826-11830.
      M. Ghaffarzadeh, P. Akhavan, Chem. Lett. 2014, 43, 1417-1419.
      S.-P. Wang, C. W. Cheung, J.-A. Ma, J. Org. Chem. 2019, 84, 13922-13934.
      A. Kumar, H. K. Akula, M. K. Lakshman, Eur. J. Org. Chem. 2010, 2709-2715.
      D. S. Barak, D. J. Dahatonde, S. U. Dighe, R. Kant, S. Batra, Org. Lett. 2020, 22, 9381-9385.
      E. G. Janzen, U. M. Oehler, Tetrahedron Lett. 1983, 24, 669-672.
      X. Wang, H. Guo, G. Xie, Y. Zhang Synth. Commun. 2004, 34, 3001-3008.
      C. W. Cheung, M. L. Ploeger, X. Hu, Nat. Commun. 2017, 8, 14878-14887.
      X. Pu, J. Hu, Y. Zhao, Z. Shi, ACS Catal. 2016, 6, 6692-6698.
      L. Hie, N. F. F. Nathel, X. Hong, Y.-F. Yang, K. N. Houk, N. K. Garg, Angew. Chem. Int. Ed. 2016, 55, 2810-2814;.
      Angew. Chem. 2016, 128, 2860-2864.
      M. L. Ploeger, A. Daru, J. N. Harvey, X. Hu, ACS Catal. 2020, 10, 2845-2854.
      L. Ling, C. Chen, M. Luo, X. Zeng, Org. Lett. 2019, 21, 1912-1916.
      C. W. Cheung, N. Shen, S.-P. Wang, A. Ullah, X. Hu, J.-A. Ma, Org. Chem. Front. 2019, 6, 756-761.
      R. N. Baruah, Indian J. Chem.- Sect. B Org. Med. Chem. 2000, 39, 300-303.
      B. H. Kim, R. Han, F. Piao, Y. M. Jun, W. Baik, B. M. Lee, Tetrahedron Lett. 2003, 44, 77-79.
      A. Bhattacharya, V. C. Purohit, V. Suarez, R. Tichkule, G. Parmer, F. Rinaldi, Tetrahedron Lett. 2006, 47, 1861-1864.
      E. Massolo, M. Pirola, A. Puglisi, S. Rossi, M. Benaglia, RSC Adv. 2020, 10, 4040-4044.
      A. E. Wahba, J. Peng, M. T. Hamann, Tetrahedron Lett. 2009, 50, 3901-3904.
      Y. Wu, L. Guo, Y. Liu, J. Xiang, J. Jiang RSC Adv. 2021, 11, 15290-15295.
      F. Xiao, Y. Liu, C. Tang, G.-J. Deng, Org. Lett. 2012, 14, 984-987.
      R. A. Jackson, W. A. Waters, J. Chem. Soc. 1960, 1653-1657.
      G. J. Deng, W. W. Chen, C.-J. Li, Adv. Synth. Catal. 2009, 351, 353-356.
      S. K. Jain, K. A. A. Kumar, S. B. Bharate, R. A. Vishwakarma, Org. Biomol. Chem. 2014, 12, 6465-6469.
       .
      S. K. Jain, S. B. Bharate, R. A. Vishwakarma, Med. Chem. 2012, 12, 632-649;.
      S. K. Jain, S. Meena, B. Singh, J. B. Bharate, P. Joshi, V. P. Singh, R. A. Vishwakarma, S. B. Bharate, RSC Adv. 2012, 2, 8929-8933.
      G. Sheng, X. Wu, X. Cai, W. Zhang, Synthesis 2015, 47, 949-954.
      J. Liu, C. Zhang, Z. Zhang, X. Wen, X. Dou, J. Wei, X. Qiu, S. Song, N. Jiao, Science 2020, 367, 281-285.
      N. Shen, S.-J. Zhai, C. W. Cheung, J.-A. Ma, Chem. Commun. 2020, 56, 9620-9623.
      C. W. Cheung, M. L. Ploeger, X. Hu, ACS Catal. 2017, 7, 7092-7096.
       .
      E. L. Baker, M. M. Yamano, Y. Zhou, S. M. Anthony, N. K. Garg, Nat. Commun. 2016, 7, 11554;.
      J. E. Dander, E. L. Baker, N. K. Garg, Chem. Sci. 2017, 8, 6433-6438.
      C. W. Cheung, J.-A. Ma, X. Hu, J. Am. Chem. Soc. 2018, 140, 6789-6792.
       .
      M. Lakshmi Kantam, R. S. Reddy, K. Srinivas, R. Chakravarti, B. Sreedhar, F. Figueras, Ch. V. Reddy, J. Mol. Catal. A: Chemical 2012, 355, 96-101;.
      X.-B. Lou, L. He, Y. Qian, Y.-M. Liu, Y. Cao, K.-N. Fana, Adv. Synth. Catal. 2011, 353, 281-286;.
      M. Li, L. Hu, X. Cao, H. Hong, J. Lu, H. Gu, Chem. Eur. J. 2011, 17, 2763-2768;.
      Z. Shokri, B. Zeynizadeh, S. A. Hosseini, J. Colloid Interface Sci. 2017, 485, 99-105;.
      B. Zeynizadeh, S. Rahmani, H. Tizhoush, Polyhedron 2020, 175, 114201;.
      B. Zeynizadeh, Z. Shokri, M. H. Galehban, Appl. Organomet. Chem. 2019, 33, e4771;.
      R. J. Rahaim Jr., R. E. Maleczka Jr., Synthesis 2006, 19, 3316-3340.
    • Grant Information:
      10283 CSIR
    • Contributed Indexing:
      Keywords: Amidation; Amide; Aminocarbonylation; Nitroarene; Transamidation
    • الرقم المعرف:
      0 (Amides)
      0 (Amines)
      0 (Carboxylic Acids)
      0 (Nitro Compounds)
    • الموضوع:
      Date Created: 20210902 Date Completed: 20211229 Latest Revision: 20211229
    • الموضوع:
      20250114
    • الرقم المعرف:
      10.1002/tcr.202100224
    • الرقم المعرف:
      34472167