N-alkylsulfonamides as useful carbon electrophiles

Synlett

Volumn 24, Issue 10, 2013, Pages 1170-1185

  Gu, Yonghong ^a   Tian, Shi Kai ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkylation; carbocations; electrophiles; heterocycles; nucleophiles; sulfonamides

Indexed keywords

ALDEHYDE; AROMATIC COMPOUND; CARBENE; CARBON; ELECTROPHILE; KETONE; N ALKYLSULFONAMIDE; NITROGEN; NUCLEOPHILE; OXYGEN; SULFINIC ACID DERIVATIVE; SULFONAMIDE; SULFUR; THIOACETIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ELECTROPHILICITY; EPIMERIZATION; FRIEDEL CRAFTS REACTION; SYNTHESIS;

EID: 84877607366     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1338460     Document Type: Article

References (74)

1. Carey F. A., Sundberg R. J. Advanced Organic Chemistry Part B: Reactions and Synthesis. 5th ed. Springer New York: 2007
2. Greene T. W., Wuts P. G. M. Protective Groups in Organic Synthesis. 3rd ed. Wiley New York: 1999
3. Escoubet S., Gastaldi S., Bertrand M. Eur. J. Org. Chem.: 2005; 3855
4. Trost B. M., Keinan E. J. Org. Chem.: 1980; 45 2741
5. Kunakova R. V., Gaisin R. L., Sirazova M. M., Dzhemilev U. M. Izv. Akad. Nauk SSSR, Ser. Khim.: 1983; 32 157; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); 1983, 32: 133
6. Murahashi S.-I, Makabe Y., Kunita K. J. Org. Chem.: 1988; 53 4489
7. Garro-Helion F., Merzouk A., Guibé F. J. Org. Chem.: 1993; 58 6109
8. Murahashi S.-I, Imada Y., Nishimura K. Tetrahedron: 1994; 50 453
9. Pawlas J., Nakao Y., Kawatsura M., Hartwig J. F. J. Am. Chem. Soc.: 2002; 124 3669
10. Zhao X., Liu D., Guo H., Liu Y., Zhang W. J. Am. Chem. Soc.: 2011; 133 19354
11. Li M.-B, Wang Y., Tian S.-K. Angew. Chem. Int. Ed.: 2012; 51 2968
12. Wu X.-S, Chen Y., Li M.-B, Zhou M.-G, Tian S.-K. J. Am. Chem. Soc.: 2012; 134 14694
13. Geng W., Zhang W.-X, Hao W., Xi Z. J. Am. Chem. Soc.: 2012; 134 20230
14. Chung K. H., Kim J. N., Ryu E. K. Tetrahedron Lett.: 1994; 35 2913
15. Seong M. R., Lee H. J., Kim J. N. Tetrahedron Lett.: 1998; 39 6219
16. Lee H. J., Seong M. R., Song H. N., Kim J. N. Bull. Korean Chem. Soc.: 1999; 20 267
17. Esquivias J., Gómez-Arrayás R., Carretero J. C. Angew. Chem. Int. Ed.: 2006; 45 629
18. Onishi Y., Ito T., Yasuda M., Baba A. Tetrahedron: 2002; 58 8227
19. Saito T., Nishimoto Y., Yasuda M., Baba A. J. Org. Chem.: 2006; 71 8516
20. Yang B.-L, Tian S.-K. Eur. J. Org. Chem.: 2007; 4646
21. Song Q.-Y, Yang B.-L, Tian S.-K. J. Org. Chem.: 2007; 72 5407
22. Keay B. A., Dibble P. W. In Comprehensive Heterocyclic Chemistry II. Vol. 2 Katritzky A. R., Rees C. W., Scriven E. F. V. Pergamon Oxford: 1996; 395
23. Brown R. C. D. Angew. Chem. Int. Ed.: 2005; 44 850
24. Kirsch S. F. Org. Biomol. Chem.: 2006; 4 2076
25. Rohr K., Mahrwald R. Org. Lett.: 2011; 13 1878
26. Yang C.-F, Shen C., Wang J.-Y, Tian S.-K. Org. Lett.: 2012; 14 3092
27. Yang C.-F, Shen C., Li H.-H, Tian S.-K. Chin. Sci. Bull.: 2012; 57 2377
28. Zheng Y., Xiong H.-Y, Nie J., Hua M.-Q, Ma J.-A. Chem. Commun.: 2012; 48 4308
29. Zhong F., Yao W., Dou X., Lu Y. Org. Lett.: 2012; 14 4018
30. Chen Y., Tian S.-K. Chin. J. Chem.: 2013; 31 37
31. Shaikh R. R., Mazzanti A., Petrini M., Bartoli G., Melchiorre P. Angew. Chem. Int. Ed.: 2008; 47 8707
32. Cozzi P. G., Benfatti F., Zoli L. Angew. Chem. Int. Ed.: 2009; 48 1313
33. Brown A. R., Kuo W.-H, Jacobsen E. N. J. Am. Chem. Soc.: 2010; 132 9286
34. Zhang L., Cui L., Li X., Li J., Luo S., Cheng J.-P. Chem. Eur. J.: 2010; 16 2045
35. Zhang L., Cui L., Li X., Li J., Luo S., Cheng J.-P. Eur. J. Org. Chem.: 2010; 4876
36. Mukherjee S., Yang J. W., Hoffmann S., List B. Chem. Rev.: 2007; 107 5471
37. Melchiorre P., Marigo M., Carlone A., Bartoli G. Angew. Chem. Int. Ed.: 2008; 47 6138
38. Pihko P. M., Majander I., Erkkilä A. Top. Curr. Chem.: 2010; 291 29
39. Duxbury D. F. Chem. Rev.: 1993; 93 381
40. Shchepinov M. S., Korshun V. A. Chem. Soc. Rev.: 2003; 32 170
41. Nair V., Thomas S., Mathew S. C., Abhilash K. G. Tetrahedron: 2006; 62 6731
42. Ke B., Qin Y., He Q., Huang Z., Wang F. Tetrahedron Lett.: 2005; 46 1751
43. Temelli B., Unaleroglu C. Tetrahedron Lett.: 2005; 46 7941
44. Soueidan M., Collin J., Gil R. Tetrahedron Lett.: 2006; 47 5467
45. Wang Y.-Q, Song J., Hong R., Li H., Deng L. J. Am. Chem. Soc.: 2006; 128 8156
46. Gao H., Katzenellenbogen J. A., Garg R., Hansch C. Chem. Rev.: 1999; 99 723
47. Alt H. G., Köppl A. Chem. Rev.: 2000; 100 1205
48. Wang B. Coord. Chem. Rev.: 2006; 250 242
49. Stang P. J., Rappopoat Z., Hanack M., Subramanian L. R. Vinyl Cations. Academic Press New York: 1979
50. Dicoordinated Carbocations. Rappoport Z., Stang P. J. Wiley Chichester: 1997
51. Yue H.-L, Wei W., Li M.-M, Yang Y.-R, Ji J.-X. Adv. Synth. Catal.: 2011; 353 3139
52. Liu Z.-Q, Zhang Y., Zhao L., Li Z., Wang J., Li H., Wu L.-M. Org. Lett.: 2011; 13 2208
53. Peng S., Wang L., Wang J. Org. Biomol. Chem.: 2012; 10 225
54. Huang G.-B, Wang X., Pan Y.-M, Wang H.-S, Yao G.-Y, Zhang Y. J. Org. Chem.: 2013; 78 2742
55. Lantaño B., Aguirre J. M., Ugliarolo E. A., Benegas M. L., Moltrasio G. Y. Tetrahedron: 2008; 64 4090
56. Li H., Li W., Liu W., He Z., Li Z. Angew. Chem. Int. Ed.: 2011; 50 2975
57. Ma S. In Modern Allene Chemistry. Vol. 2 Krause N., Hashmi A. S. K. Wiley-VCH Weinheim: 2004; 595
58. Ma S. Pure Appl. Chem.: 2007; 79 261
59. Ma S. Acc. Chem. Res.: 2009; 42 1679
60. Enders D., Narine A. A., Toulgoat F., Bisschops T. Angew. Chem. Int. Ed.: 2008; 47 5661
61. Sun F.-L, Zheng X.-J, Gu Q., He Q.-L, You S.-L. Eur. J. Org. Chem.: 2010; 47
62. Akiyama T. Chem. Rev.: 2007; 107 5744
63. Terada M. Chem. Commun.: 2008; 4097
64. Terada M. Synthesis: 2010; 1929
65. Yu J., Shi F., Gong L.-Z. Acc. Chem. Res.: 2011; 44 1156
66. Keith J. M., Larrow J. F., Jacobsen E. N. Adv. Synth. Catal.: 2001; 343 5
67. Vedejs E., Jure M. Angew. Chem. Int. Ed.: 2005; 44 3974
68. Kang Q., Zhao Z.-A, You S.-L. J. Am. Chem. Soc.: 2007; 129 1484
69. Xu F., Huang D., Han C., Shen W., Lin X., Wang Y. J. Org. Chem.: 2010; 75 8677
70. Xing C.-H, Liao Y.-X, Ng J., Hu Q.-S. J. Org. Chem.: 2011; 76 4125
71. Jia Y.-X, Zhong J., Zhu S.-F, Zhang C.-M, Zhou Q.-L. Angew. Chem. Int. Ed.: 2007; 46 5565
72. Lin J.-H, Xiao J.-C. Eur. J. Org. Chem.: 2011; 4536
73. Cheng D.-J, Wu H.-B, Tian S.-K. Org. Lett.: 2011; 13 5636
74. Cheng D.-J, Tian Y., Tian S.-K. Adv. Synth. Catal.: 2012; 354 995