Citation: Jiashun Cheng, Pinhong Chen, Guosheng Liu. Pd-catalyzed intramolecular aminofluorination of allylic sulfamides[J]. Chinese Journal of Catalysis, ;2015, 36(1): 40-47. doi: 10.1016/S1872-2067(14)60164-9 shu

Pd-catalyzed intramolecular aminofluorination of allylic sulfamides

1.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Corresponding author: Guosheng Liu,
Received Date: 19 May 2014
Available Online: 9 June 2014
Fund Project: 国家重点基础研究发展计划(973计划, 2011CB808700) (973计划, 2011CB808700) 国家自然科学基金(21225210, 20923005和21121062) (21225210, 20923005和21121062) 上海市科学技术委员会(11JC1415000) (11JC1415000)

A facile Pd-catalyzed intramolecular aminofluorination reaction of allylic sulfamides was developed that can be used to prepare fluorinated 1,3-diamine derivatives. Acetic acid was essential for regulation to give the major 6-endo cyclization products.
- Palladium-catalyzed,
- Aminofluorination,
- Alkene,
- Fluorinated 1,3-diamine,
- 6-Endo cyclization
1. [1]
  [1] Filler R, Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry. Amsterdam: Elsevier, 1982. 1
2. [2]
  [2] Welch J T, Eswarakrishman S. Fluorine in Bioorganic Chemistry. New York: Wiley, 1991. 1
3. [3]
  [3] Miyake H. In: Banks R E, Smart B E, Tatlow J C ed. Organofluorine Chemistry: Principles and Commercial Applications. New York: Plenum Press, 1994. 555
4. [4]
  [4] Nyffeler P T, Duron S G, Burkart M D, Vincent S P, Wong C H. Angew Chem Int Ed, 2005, 44: 192
5. [5]
  [5] Shimizu M, Hiyama T. Angew Chem Int Ed, 2005, 44: 214
6. [6]
  [6] Pihko P M. Angew Chem Int Ed, 2006, 45: 544
7. [7]
  [7] Petrov V A. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications. Hoboken, NJ: John Wiley & Sons, Inc, 2009
8. [8]
  [8] Nosova E V, Lipunova G N, Charushin V N, Chupakhin O N. J Fluorine Chem, 2010, 131: 1267
9. [9]
  [9] Zhu S Z, Wang Y L, Peng W M, Song L P, Jin G F. Curr Org Chem, 2002, 6: 1057
10. [10]
  [10] Silvester M J. Aldrich Acta, 1991, 24: 31
11. [11]
  [11] Kwiatkowski P, Beeson T D, Conrad J C, MacMillan D W C. J Am Chem Soc, 2011, 133: 1738
12. [12]
  [12] Kishi Y, Nagura H, Inagi S, Fuchigami T. Chem Commun, 2008: 3876
13. [13]
  [13] Fustero S, Catalan S, Sanchez-Rosello M, Simon-Fuentes A, del Pozo C. Org Lett, 2010, 12: 3484
14. [14]
  [14] Jensen K H, Sigman M S. Org Biomol Chem, 2008, 6: 4083
15. [15]
  [15] Kotov V, Scarborough C C, Stahl S S. Inorg Chem, 2007, 46: 1910
16. [16]
  [16] Wu T, Yin G Y, Liu G S. J Am Chem Soc, 2009, 131: 16354
17. [17]
  [17] Wu T, Cheng J S, Chen P H, Liu G S. Chem Commun, 2013, 49: 8707
18. [18]
  [18] Zhu H T, Liu G S. Acta Chim Sinica (朱海涛, 刘国生. 化学学报), 2012, 70: 2404
19. [19]
  [19] Qiu S F, Xu T, Zhou J, Guo Y L, Liu G S. J Am Chem Soc, 2010, 132: 2856
20. [20]
  [20] Xu T, Qiu S F, Liu G S. Chin J Chem (徐涛, 邱水发, 刘国生. 中国化学), 2011, 29: 2785
21. [21]
  [21] Xu T, Mu X, Peng H H, Liu G S. Angew Chem Int Ed, 2011, 50: 8176
22. [22]
  [22] Xu T, Liu G S. Org Lett, 2012, 14: 5416;
23. [23]
  [23] Liu Q L, Wu Y C, Chen P H, Liu G S. Org Lett, 2013, 15: 6210
24. [24]
  [24] Qian J Q, Liu Y K, Zhu J, Jiang B, Xu Z Y. Org Lett, 2011, 13: 4220
25. [25]
  [25] Li Z D, Song L Y, Li C Z. J Am Chem Soc, 2013, 135: 4640
26. [26]
  [26] Wang Q, Zhong W H, Wei X, Ning M H, Meng X B, Li Z J. Org Biomol Chem, 2012, 10: 8566
27. [27]
  [27] Huang H T, Lacy T C, Blachut B, Ortiz Jr G X, Wang Q. Org Lett, 2013, 15: 1818
28. [28]
  [28] Cui J, Jia Q, Feng R Z, Liu S S, He T, Zhang C. Org Lett, 2014, 16: 1442
29. [29]
  [29] Kong W Q, Feige P, de Haro T, Nevado C. Angew Chem Int Ed, 2013, 52: 2469
30. [30]
  [30] Shuntona H P, Früeh N, Wang Y M, Rauniyar V, Toste F D. Angew Chem Int Ed, 2013, 52: 7724
31. [31]
  [31] Eickmeier C, Peters S, Fuchs K, Heine N, Handschuh S, Dorner- Ciossek C, Klinder K, Kostka, M. US Patent 5 006 939. 2006
32. [32]
  [32] Martinez A, Castro A, Gil C, Miralpeix M, Segarra V, Domenech T, Beleta J, Palacios J M, Ryder H, Miro X, Bonet C, Casacuberta J M, Azorin F, Pina B, Puigdomenech P. J Med Chem, 2000, 43: 683
33. [33]
  [33] Armarego W L F. Purification of Laboratory Chemicals. Amsterdam: Elsevier, 1997
34. [34]
  [34] McDonald R I, Stahl S S. Angew Chem Int Ed, 2010, 49: 5529
35. [35]
  [35] Yin G Y, Wu T, Liu G S. Chem Eur J, 2012, 18: 451
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