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J Am Chem Soc. 2019 Jan 16;141(2):998-1009. doi: 10.1021/jacs.8b11062. Epub 2018 Dec 28.

Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

Journal of the American Chemical Society

Yernaidu Reddi, Cheng-Che Tsai, Carolina M Avila, F Dean Toste, Raghavan B Sunoj

Affiliations

  1. Department of Chemistry , Indian Institute of Technology Bombay , Powai, Mumbai 400076 , India.
  2. Department of Chemistry , University of California Berkeley , Berkeley , California 94720 , United States.

PMID: 30562010 PMCID: PMC6482286 DOI: 10.1021/jacs.8b11062

Abstract

The use of more than one catalyst in one-pot reaction conditions has become a rapidly evolving protocol in the development of asymmetric catalysis. The lack of molecular insights on the mechanism and enantioselectivity in dual-catalytic reactions motivated the present study focusing on an important catalytic asymmetric Heck-Matsuda cross-coupling. A comprehensive density functional theory (M06 and B3LYP-D3) investigation of the coupling between a spirocyclic cyclopentene and 4-fluorophenyl diazonium species under a dual-catalytic condition involving Pd

References

  1. Acta Crystallogr B. 1999 Aug 1;55(Pt 4):563-572 - PubMed
  2. J Am Chem Soc. 2006 Mar 15;128(10):3355-65 - PubMed
  3. Science. 2007 Jul 27;317(5837):496-9 - PubMed
  4. J Am Chem Soc. 2007 Sep 19;129(37):11336-7 - PubMed
  5. J Phys Chem A. 2008 Jul 3;112(26):6032-41 - PubMed
  6. J Am Chem Soc. 2008 Aug 6;130(31):10187-98 - PubMed
  7. Nature. 2008 Sep 18;455(7211):309-13 - PubMed
  8. J Phys Chem B. 2009 May 7;113(18):6378-96 - PubMed
  9. J Am Chem Soc. 2010 Mar 17;132(10):3304-11 - PubMed
  10. J Chem Phys. 2010 Apr 21;132(15):154104 - PubMed
  11. Biophys J. 2010 May 19;98(10):L47-9 - PubMed
  12. Proc Natl Acad Sci U S A. 2010 Nov 30;107(48):20678-85 - PubMed
  13. Acc Chem Res. 2011 Feb 15;44(2):101-10 - PubMed
  14. Angew Chem Int Ed Engl. 2011 Oct 4;50(41):9752-5 - PubMed
  15. Science. 2011 Dec 23;334(6063):1681-4 - PubMed
  16. J Am Chem Soc. 2012 Feb 29;134(8):3615-8 - PubMed
  17. Chem Sci. 2012 Jan 1;2012(3):633-658 - PubMed
  18. Chemistry. 2012 Aug 6;18(32):9955-64 - PubMed
  19. Nat Chem. 2012 Jul 24;4(8):603-14 - PubMed
  20. Chem Soc Rev. 2013 Feb 7;42(3):1337-78 - PubMed
  21. Angew Chem Int Ed Engl. 2013 Jan 7;52(2):534-61 - PubMed
  22. Science. 2012 Dec 14;338(6113):1455-8 - PubMed
  23. Angew Chem Int Ed Engl. 2013 Jan 7;52(2):518-33 - PubMed
  24. J Chem Phys. 2013 Jan 7;138(1):014501 - PubMed
  25. J Org Chem. 2013 May 3;78(9):4373-85 - PubMed
  26. J Am Chem Soc. 2013 Jun 26;135(25):9255-8 - PubMed
  27. J Am Chem Soc. 2014 Jan 22;136(3):986-98 - PubMed
  28. J Am Chem Soc. 2014 Feb 5;136(5):1960-7 - PubMed
  29. Angew Chem Int Ed Engl. 2014 Feb 24;53(9):2282-5 - PubMed
  30. Nature. 2014 Apr 17;508(7496):340-4 - PubMed
  31. Acc Chem Res. 2014 Aug 19;47(8):2365-77 - PubMed
  32. J Org Chem. 2014 Aug 15;79(16):7600-6 - PubMed
  33. Chem Rev. 2014 Sep 24;114(18):9047-153 - PubMed
  34. Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13049-53 - PubMed
  35. Chem Sci. 2015 Jan 1;6(1):170-173 - PubMed
  36. Science. 2015 Feb 13;347(6223):737-43 - PubMed
  37. J Am Chem Soc. 2015 Mar 11;137(9):3213-3216 - PubMed
  38. Angew Chem Int Ed Engl. 2015 May 11;54(20):6024-7 - PubMed
  39. Chemistry. 2015 Jul 27;21(31):11152-7 - PubMed
  40. Org Biomol Chem. 2015 Aug 14;13(30):8116-62 - PubMed
  41. Chem Rev. 2015 Sep 9;115(17):9587-652 - PubMed
  42. Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14036-9 - PubMed
  43. J Org Chem. 2016 Mar 4;81(5):2010-8 - PubMed
  44. J Am Chem Soc. 2016 Mar 23;138(11):3863-75 - PubMed
  45. Acc Chem Res. 2016 May 17;49(5):1019-28 - PubMed
  46. Acc Chem Res. 2016 May 17;49(5):1061-9 - PubMed
  47. Acc Chem Res. 2016 May 17;49(5):1029-41 - PubMed
  48. Acc Chem Res. 2016 Jun 21;49(6):1311-9 - PubMed
  49. J Am Chem Soc. 2016 Jun 29;138(25):7910-7 - PubMed
  50. Acc Chem Res. 2016 Jun 21;49(6):1279-91 - PubMed
  51. Chemistry. 2016 Aug 1;22(32):11205-9 - PubMed
  52. Chem Soc Rev. 2016 Nov 7;45(22):6093-6107 - PubMed
  53. Org Biomol Chem. 2016 Oct 12;14(40):9476-9480 - PubMed
  54. Angew Chem Int Ed Engl. 2016 Dec 23;55(52):16153-16155 - PubMed
  55. J Am Chem Soc. 2016 Dec 14;138(49):15877-15880 - PubMed
  56. J Org Chem. 2017 Jan 20;82(2):1127-1135 - PubMed
  57. J Am Chem Soc. 2017 Feb 1;139(4):1412-1415 - PubMed
  58. Nature. 2017 Mar 29;543(7647):637-646 - PubMed
  59. J Am Chem Soc. 2017 Apr 26;139(16):5627-5639 - PubMed
  60. Angew Chem Int Ed Engl. 2017 May 15;56(21):5806-5811 - PubMed
  61. Angew Chem Int Ed Engl. 2017 Aug 14;56(34):10070-10086 - PubMed
  62. Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7209-7212 - PubMed
  63. J Am Chem Soc. 2017 Jul 5;139(26):8886-8896 - PubMed
  64. J Am Chem Soc. 2017 Sep 13;139(36):12688-12695 - PubMed
  65. Angew Chem Int Ed Engl. 2018 Jan 8;57(2):589-593 - PubMed
  66. J Org Chem. 2018 Feb 16;83(4):2198-2209 - PubMed
  67. J Am Chem Soc. 2018 Feb 21;140(7):2629-2642 - PubMed
  68. Chem Rev. 2018 Feb 28;118(4):2249-2295 - PubMed
  69. J Am Chem Soc. 2018 Mar 14;140(10):3551-3554 - PubMed
  70. Chemistry. 2018 Aug 9;24(45):11738-11747 - PubMed
  71. J Am Chem Soc. 2018 May 23;140(20):6203-6207 - PubMed
  72. Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12067-12070 - PubMed
  73. Chem Sci. 2018 Jun 25;9(28):6126-6133 - PubMed
  74. Chem Sci. 2018 Aug 3;9(35):7153-7158 - PubMed

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