Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

Chemical Communications

Volumn 52, Issue 12, 2016, Pages 2639-2642

  Pace, Vittorio ^a   Pelosi, Azzurra ^a,b   Antermite, Daniele ^a   Rosati, Ornelio ^b   Curini, Massimo ^b   Holzer, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; BROMINE; CARBENOID; DISULFIDE; ELECTROPHILE; LITHIUM; ORGANOLITHIUM COMPOUND; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; COVALENT BOND; ELECTROPHILICITY; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; SIMMONS SMITH REACTION;

EID: 84957569810     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc10280d     Document Type: Article

References (73)

1. J. J. Li, Name Reactions for Homologation, Wiley, Hoboken, 2009
2. The Practice of Medicinal Chemistry, ed., C. G. Wermuth, Academic Press, 2015
3. M. Burns S. Essafi J. R. Bame S. P. Bull M. P. Webster S. Balieu J. W. Dale C. P. Butts J. N. Harvey V. K. Aggarwal Nature 2014 513 183
4. F. Arndt B. Eistert Ber. Dtsch. Chem. Ges. 1935 68 200
5. T. H. Black Aldrichimica Acta 1983 16 3
6. M. Regitz and G. Maas, Diazo Compounds-Properties and Synthesis, Academic Press, Orlando, 1986
7. G. Maas Angew. Chem., Int. Ed. 2009 48 8186
8. A. Ford H. Miel A. Ring C. N. Slattery A. R. Maguire M. A. McKervey Chem. Rev. 2015 115 9981
9. H. E. Simmons R. D. Smith J. Am. Chem. Soc. 1958 80 5323
10. A. B. Charette and A. Beauchemin, in Organic Reactions, John Wiley & Sons, Inc., 2004
11. G. Boche J. C. W. Lohrenz Chem. Rev. 2001 101 697
12. V. Capriati S. Florio Chem.-Eur. J. 2010 16 4152
13. V. Capriati, Contemporary Carbene Chemistry, John Wiley & Sons, Inc 2013 p. 325
14. M. Braun, in The Chemistry of Organolithium Compounds, ed., Z. Rappoport, and, I. Marek, John Wiley and Sons, Chichester, 2004, vol. 1, p. 829
15. V. Pace Aust. J. Chem. 2014 67 311
16. T. Satoh Heterocycles 2012 85 1
17. T. Satoh Chem. Soc. Rev. 2007 36 1561
18. R. H. V. Nishimura V. E. Murie R. A. Soldi G. C. Clososki Synthesis 2015 1455
19. R. H. V. Nishimura F. T. Toledo J. L. C. Lopes G. C. Clososki Tetrahedron Lett. 2013 54 287
20. C. Kupper S. Molitor V. H. Gessner Organometallics 2014 33 347
21. S. Molitor J. Becker V. H. Gessner J. Am. Chem. Soc. 2014 136 15517
22. S. Molitor K.-S. Feichtner C. Kupper V. H. Gessner Chem.-Eur. J. 2014 20 10752
23. S. Molitor V. H. Gessner Synlett 2015 861
24. V. Pace L. Castoldi W. Holzer J. Org. Chem. 2013 78 7764
25. V. Pace L. Castoldi W. Holzer Chem. Commun. 2013 49 8383
26. V. Pace W. Holzer G. Verniest A. R. Alcántara N. De Kimpe Adv. Synth. Catal. 2013 355 919
27. V. Pace L. Castoldi A. D. Mamuye W. Holzer Synthesis 2014 2897
28. A. D. Mamuye L. Castoldi U. Azzena W. Holzer V. Pace Org. Biomol. Chem. 2015 13 1969
29. V. Pace L. Castoldi A. D. Mamuye T. Langer W. Holzer Adv. Synth. Catal. 2016 10.1002/adsc.201500840
30. A. Wieczorek F. Hammerschmidt J. Org. Chem. 2012 77 10021
31. J. M. Concellon H. Rodríguez-Solla P. L. Bernad C. Simal J. Org. Chem. 2009 74 2452
32. D. C. Kapeller F. Hammerschmidt J. Am. Chem. Soc. 2008 130 2329
33. T. Onishi T. Nakano N. Hirose M. Nakazawa K. Izawa Tetrahedron Lett. 2001 42 5887
34. J. Barluenga B. Baragaña J. M. Concellón J. Org. Chem. 1995 60 6696
35. V. Pace L. Castoldi M. Pregnolato Mini-Rev. Med. Chem. 2013 13 988
36. L. Degennaro F. Fanelli A. Giovine R. Luisi Adv. Synth. Catal. 2015 357 21
37. S. Balieu G. E. Hallett M. Burns T. Bootwicha J. Studley V. K. Aggarwal J. Am. Chem. Soc. 2015 137 4398
38. C. R. Emerson L. N. Zakharov P. R. Blakemore Chem.-Eur. J. 2013 19 16342
39. R. P. Sonawane V. Jheengut C. Rabalakos R. Larouche-Gauthier H. K. Scott V. K. Aggarwal Angew. Chem., Int. Ed. 2011 50 3760
40. P. R. Blakemore S. P. Marsden H. D. Vater Org. Lett. 2006 8 773
41. P. R. Blakemore M. S. Burge J. Am. Chem. Soc. 2007 129 3068
42. D. S. Matteson D. Majumdar J. Am. Chem. Soc. 1980 102 7588
43. S. Dixon S. M. Fillery A. Kasatkin D. Norton E. Thomas R. J. Whitby Tetrahedron 2004 60 1401
44. T. Boddaert C. François L. Mistico O. Querolle L. Meerpoel P. Angibaud M. Durandetti J. Maddaluno Chem.-Eur. J. 2014 20 10131
45. M. Pasco N. Gilboa T. Mejuch I. Marek Organometallics 2013 32 942
46. J. M. Concellón H. Cuervo R. Fernández-Fano Tetrahedron 2001 57 8983
47. K. M. Sadhu D. S. Matteson Tetrahedron Lett. 1986 27 795
48. T. J. Michnick D. S. Matteson Synlett 1991 631
49. R. Tarhouni B. Kirschleger M. Rambaud J. Villieras Tetrahedron Lett. 1984 25 835
50. M. Hutchings D. Moffat N. S. Simpkins Synlett 2001 661
51. J. M. Concellón H. Rodríguez-Solla C. Simal Org. Lett. 2008 10 4457
52. L. Field C. H. Banks J. Org. Chem. 1975 40 2774
53. E. J. Corey M. Chaykovsky J. Am. Chem. Soc. 1962 84 867
54. Y. G. Gololobov A. N. Nesmeyanov V. P. lysenko I. E. Boldeskul Tetrahedron 1987 43 2609
55. L. Field H.-K. Chu J. Org. Chem. 1977 42 1768
56. N. Petragnani G. Schill Chem. Ber. 1970 103 2271
57. S. Avolio C. Malan I. Marek P. Knochel Synlett 1999 1820
58. Lithium Compounds in Organic Synthesis: From Fundamentals to Applications, ed., R. Luisi, and, V. Capriati, Wiley-VCH, Weinheim, 2014
59. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Oxford, 2002
60. T. Onishi N. Hirose T. Nakano M. Nakazawa K. Izawa Tetrahedron Lett. 2001 42 5883
61. W. Gohring S. Gokhale H. Hilpert F. Roessler M. Schlageter P. Vogt Chimia 1996 50 532
62. D. Savoia G. Alvaro R. Di Fabio A. Gualandi C. Fiorelli J. Org. Chem. 2006 71 9373
63. M. Giannerini M. Fañanás-Mastral B. L. Feringa Nat. Chem. 2013 5 667
64. M. Giannerini V. Hornillos C. Vila M. Fañanás-Mastral B. L. Feringa Angew. Chem., Int. Ed. 2013 52 13329
65. V. Hornillos M. Giannerini C. Vila M. Fañanás-Mastral B. L. Feringa Org. Lett. 2013 15 5114
66. C. Vila M. Giannerini V. Hornillos M. Fañanás-Mastral B. L. Feringa Chem. Sci. 2014 5 1361
67. V. Pace R. Luisi ChemCatChem 2014 6 1516
68. V. Capriati F. M. Perna A. Salomone Dalton Trans. 2014 43 14204
69. J. D. Firth P. O'Brien ChemCatChem 2015 7 395
70. S. Nahm S. M. Weinreb Tetrahedron Lett. 1981 22 3815
71. S. Balasubramaniam I. S. Aidhen Synthesis 2008 3707
72. S. Saito T. Tsubogo S. Kobayashi J. Am. Chem. Soc. 2007 129 5364
73. T. Tsubogo S. Saito K. Seki Y. Yamashita S. Kobayashi J. Am. Chem. Soc. 2008 130 13321