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Natural products and bioprospecting
Aug, 2021;11 (4): 379-404.

α-C(sp)-H Arylation of Cyclic Carbonyl Compounds.

Mei Wang, Wei Wang, Dashan Li, Wen-Jing Wang, Rui Zhan, Li-Dong Shao
Author Information
  1. Mei Wang: Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650050, China.
  2. Wei Wang: Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650050, China.
  3. Dashan Li: Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650050, China.
  4. Wen-Jing Wang: Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650050, China.
  5. Rui Zhan: School of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, 650050, China. sunnyzhanrui@126.com.
  6. Li-Dong Shao: Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650050, China. shaolidong@ynutcm.edu.cn. ORCID
PMID: 34097248 DOI: 10.1007/s13659-021-00312-1

Abstract

α-C(sp)-H arylation is an important type of C-H functionalization. Various biologically significant natural products, chemical intermediates, and drugs have been effectively prepared via C-H functionalization. Cyclic carbonyl compounds comprise of cyclic ketones, enones, lactones, and lactams. The α-C(sp)-H arylation of these compounds have been exhibited high efficiency in forming C(sp)-C(sp) bonds, played a crucial role in organic synthesis, and attracted majority of interests from organic and medicinal communities. This review focused on the most significant advances including methods, mechanism, and applications in total synthesis of natural products in the field of α-C(sp)-H arylations of cyclic carbonyl compounds in recent years.

Keywords

C-H functionalization Cyclic carbonyl compounds α-C(sp3)-H arylation

References

  1. J Am Chem Soc. 2011 Apr 20;133(15):5802-5 [PMID: 21443226]
  2. J Org Chem. 1996 Jun 14;61(12):4080-4086 [PMID: 11667286]
  3. J Org Chem. 2019 Oct 4;84(19):12664-12671 [PMID: 31498620]
  4. J Am Chem Soc. 2018 Jun 20;140(24):7605-7610 [PMID: 29716194]
  5. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2559-63 [PMID: 26840218]
  6. Angew Chem Int Ed Engl. 2018 Jun 25;57(26):7673-7677 [PMID: 29709091]
  7. Chem Commun (Camb). 2006 Apr 7;(13):1413-5 [PMID: 16550284]
  8. Org Lett. 2008 Apr 3;10(7):1413-5 [PMID: 18321119]
  9. Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5443-5446 [PMID: 30884052]
  10. J Am Chem Soc. 2002 Feb 20;124(7):1261-8 [PMID: 11841295]
  11. Angew Chem Int Ed Engl. 2013 May 27;52(22):5807-12 [PMID: 23610055]
  12. Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12328-12332 [PMID: 30074668]
  13. J Am Chem Soc. 2004 Jun 23;126(24):7450-1 [PMID: 15198586]
  14. Chem Commun (Camb). 2018 Dec 18;55(1):119-122 [PMID: 30516178]
  15. Chem Sci. 2019 Jan 22;10(10):3049-3053 [PMID: 30996886]
  16. Chem Commun (Camb). 2014 May 25;50(40):5230-2 [PMID: 24280974]
  17. Org Lett. 2019 Dec 6;21(23):9286-9290 [PMID: 31593479]
  18. J Am Chem Soc. 2011 Oct 19;133(41):16330-3 [PMID: 21916501]
  19. Org Lett. 2003 May 29;5(11):1915-8 [PMID: 12762685]
  20. Angew Chem Int Ed Engl. 2015 Mar 23;54(13):4075-8 [PMID: 25650559]
  21. Org Lett. 2016 Aug 19;18(16):3948-51 [PMID: 27486900]
  22. Org Lett. 2009 Apr 2;11(7):1543-6 [PMID: 19254009]
  23. Org Biomol Chem. 2015 May 7;13(17):4837-40 [PMID: 25806855]
  24. J Am Chem Soc. 2016 Dec 14;138(49):15980-15986 [PMID: 27960323]
  25. J Am Chem Soc. 2011 Feb 23;133(7):2088-91 [PMID: 21268578]
  26. J Am Chem Soc. 2005 Nov 9;127(44):15394-6 [PMID: 16262402]
  27. J Am Chem Soc. 2017 Nov 22;139(46):16486-16489 [PMID: 29116769]
  28. Chem Rev. 2017 Jul 12;117(13):8754-8786 [PMID: 28697604]
  29. J Am Chem Soc. 2012 Aug 29;134(34):13954-7 [PMID: 22889065]
  30. J Org Chem. 2009 Jul 17;74(14):5032-40 [PMID: 19472991]
  31. Org Lett. 2009 Feb 5;11(3):555-8 [PMID: 19117400]
  32. Org Lett. 2019 May 17;21(10):3678-3681 [PMID: 31038317]
  33. J Am Chem Soc. 2014 Dec 31;136(52):17962-5 [PMID: 25496352]
  34. Angew Chem Int Ed Engl. 2008;47(1):177-80 [PMID: 18033712]
  35. Angew Chem Int Ed Engl. 2018 Mar 1;57(10):2707-2711 [PMID: 29318758]
  36. Angew Chem Int Ed Engl. 2019 Mar 22;58(13):4297-4301 [PMID: 30677201]
  37. Nature. 2019 Mar;567(7747):223-228 [PMID: 30867606]
  38. Angew Chem Int Ed Engl. 2014 Jun 10;53(24):6220-3 [PMID: 24802937]
  39. J Am Chem Soc. 2008 Jul 23;130(29):9613-20 [PMID: 18588302]
  40. Org Lett. 2021 Feb 5;23(3):920-924 [PMID: 33501833]
  41. J Am Chem Soc. 2020 Feb 12;142(6):3269-3274 [PMID: 31992040]
  42. Bioorg Med Chem Lett. 2002 Apr 8;12(7):1023-6 [PMID: 11909708]
  43. Angew Chem Int Ed Engl. 2010;49(4):676-707 [PMID: 20058282]
  44. J Org Chem. 2018 Sep 7;83(17):10166-10174 [PMID: 30032617]
  45. J Am Chem Soc. 2003 Feb 12;125(6):1587-94 [PMID: 12568619]
  46. J Am Chem Soc. 2016 Apr 27;138(16):5198-201 [PMID: 27078124]
  47. Nat Rev Chem. 2017;1: [PMID: 29034333]
  48. Nat Chem. 2020 May;12(5):489-496 [PMID: 32152476]
  49. J Am Chem Soc. 2005 Mar 23;127(11):3670-1 [PMID: 15771481]
  50. Nature. 2007 Mar 22;446(7134):404-8 [PMID: 17377577]
  51. Org Lett. 2016 Dec 16;18(24):6488-6491 [PMID: 27978660]
  52. Org Lett. 2019 Jul 19;21(14):5757-5761 [PMID: 31264879]
  53. Planta Med. 2005 Jan;71(1):72-6 [PMID: 15678377]
  54. Org Lett. 2015 Aug 7;17(15):3838-41 [PMID: 26200165]
  55. Org Lett. 2002 Nov 14;4(23):4053-6 [PMID: 12423084]
  56. Chem Asian J. 2017 Apr 4;12(7):734-743 [PMID: 28169505]
  57. J Am Chem Soc. 2015 Jan 28;137(3):1330-40 [PMID: 25594682]
  58. Angew Chem Int Ed Engl. 2019 May 13;58(20):6659-6662 [PMID: 30835916]
  59. Nat Chem. 2020 Jan;12(1):76-81 [PMID: 31863014]
  60. Angew Chem Int Ed Engl. 2015 Dec 7;54(50):15294-8 [PMID: 26486569]
  61. Nat Chem. 2020 May;12(5):459-467 [PMID: 32203440]
  62. Science. 2013 Jan 4;339(6115):59-63 [PMID: 23288535]
  63. J Am Chem Soc. 2018 Oct 31;140(43):13988-14009 [PMID: 30185033]
  64. Org Lett. 2017 Mar 17;19(6):1390-1393 [PMID: 28263071]
  65. J Org Chem. 2005 Jun 10;70(12):4720-5 [PMID: 15932310]
  66. Org Lett. 2020 Jun 19;22(12):4602-4607 [PMID: 32484358]
  67. Science. 2006 Apr 7;312(5770):67-72 [PMID: 16601184]
  68. Chem Rev. 2020 Feb 12;120(3):1788-1887 [PMID: 31904219]
  69. Acc Chem Res. 2020 Feb 18;53(2):300-310 [PMID: 31939278]
  70. J Am Chem Soc. 2002 Apr 10;124(14):3500-1 [PMID: 11929227]
  71. Org Lett. 2017 Jun 16;19(12):3167-3170 [PMID: 28570070]
  72. Angew Chem Int Ed Engl. 2013 Sep 23;52(39):10245-9 [PMID: 24019290]
  73. Chem Rev. 2010 Feb 10;110(2):1082-146 [PMID: 19610600]
  74. Science. 2014 Jul 4;345(6192):68-72 [PMID: 24994648]
  75. J Am Chem Soc. 2008 Jan 9;130(1):195-200 [PMID: 18076166]
  76. J Am Chem Soc. 2007 Feb 7;129(5):1034-5 [PMID: 17263376]
  77. Acc Chem Res. 2003 Apr;36(4):234-45 [PMID: 12693921]
  78. Nat Chem. 2019 Mar;11(3):213-221 [PMID: 30559371]
  79. Angew Chem Int Ed Engl. 2007;46(29):5515-9 [PMID: 17523204]
  80. J Am Chem Soc. 2011 Sep 7;133(35):13782-5 [PMID: 21848265]
  81. Nature. 2020 Apr;580(7805):621-627 [PMID: 32179876]
  82. Angew Chem Int Ed Engl. 2013 Jul 8;52(28):7317-20 [PMID: 23740529]
  83. J Am Chem Soc. 2009 Jul 29;131(29):9900-1 [PMID: 19580273]
  84. Org Lett. 2017 Mar 3;19(5):1220-1223 [PMID: 28231008]

Grants

  1. 81960631/National Science of Foundation of China
  2. 202001AS070038/Yunnan Fundamental Research Project
  3. R. Zhan and L.-D Shao/Top Young Talent of Ten Thousand Talents Program of Yunnan Province
  4. 2019YZG03/the Start-up Fund of Yunnan University of Chinese Medicine
Journal Article Review

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Created with Highcharts 10.0.0spα-C-HcompoundsarylationC-HfunctionalizationCycliccarbonylsignificantnaturalproductscyclicorganicsynthesisimportanttypeVariousbiologicallychemicalintermediatesdrugseffectivelypreparedviacompriseketonesenoneslactoneslactamsexhibitedhighefficiencyformingC-CbondsplayedcrucialroleattractedmajorityinterestsmedicinalcommunitiesreviewfocusedadvancesincludingmethodsmechanismapplicationstotalfieldarylationsrecentyearsArylationCarbonylCompoundssp3

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