Carbon-Carbon Bond Forming Reactions by using Bistrifluoro-methanesulfonimide

 

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Abstract

Bistrifluoromethanesulfonimide has been used to catalyze C-C bond forming reactions such as Friedel-Crafts, Mukaiyama, 1,2-addition and 1,4-addition as well as C-glycosidation reactions.

References

• 1 Jacquelain J. Ann. Chim. Phys.  1843,  8:  293 
  Google Scholar
• 2 Foropoulos J. Desmarteau DD. Inorg. Chem.  1984,  23:  3720 
  CrossrefGoogle Scholar
• 3 Desmarteau DD. Witz M. J. Fluorine Chem.  1991,  52:  7 
  Google Scholar
• 4 Ruff JK. Inorg. Chem.  1965,  4:  1444 
  CrossrefGoogle Scholar
• 5 Rode BM. Engelbrecht A. Schant Z. J. Phys. Chem.  1973,  253:  17 
  Google Scholar
• 6 Heaney H. Comprehensive Organic Synthesis   Trost BM. Fleming I. Pergamon Press; Oxford: 1991.  p.733 
  Google Scholar
• 7 Olah A. Friedel-Crafts Chemistry   Wiley Interscience; New York: 1973. 
  Google Scholar
• 8 Mukaiyama T. Ohno T. Nishimura T. Suda S. Kobayashi S. Chem. Lett.  1991,  1059 
  Google Scholar
• 9 Hachiya I. Moriwaki M. Kobayashi S. Tetrahedron Lett.  1995,  36:  409 
  CrossrefGoogle Scholar
• 10 Kawada A. Mitamura S. Kobayashi S. Synlett  1994,  545 
  Article in Thieme ConnectGoogle Scholar
• 11 Kamada A. Mitamura S. Kobayashi S. J. Chem. Soc., Chem. Commun.  1993,  1157 
  CrossrefGoogle Scholar
• 12 Inanaga J. Sugimoto Y. Hanamoto T. New J. Chem.  1995,  19:  707 
  Google Scholar
• 13a Mikami K, Kotera O, Motoyarna Y, Maruta M, and Sakaguchi H. inventors; Jpn. Kokai Tokkyo Koho  JP 07 341 334. 
• 13b Mikami K, Kotera O, Motoyarna Y, Maruta M, and Sakaguchi H. inventors; Jpn. Kokai Tokkyo Koho  JP 01 176 081.  ; (to Centra Glass)
• 14 Ishihara K. Kubota M. Yamamoto H. Synlett  1996,  1045 
  Article in Thieme ConnectGoogle Scholar
• 15 Ishii A. Kotera O. Mikami K. Synlett  1997,  1145 
  Article in Thieme ConnectGoogle Scholar
• 16 Mukaiyama T. Angew. Chem., Int. Ed. Engl.  1977,  16:  817 ; and references cited therein
  CrossrefGoogle Scholar
• 17 Gennari C. Comprehensive Organic Synthesis   Trost BM. Fleming I. Heathcock CH. Pergamon Press; Oxford: 1991.  p.629 
  Google Scholar
• 18a

  Representative Procedure of the TFSI-H catalyzed Mukaiyama cross-aldol reaction: To a solution of 11 (851 mg, 5.00 mmol) and 2,2-dimethoxypropane (624 mg, 6.00 mmol) in CH₂Cl₂ at -78 °C, was added dropwise TFSI-H (500 µL, 0.5 M solution in CH₂Cl₂, 0.025 mmol, 5 mol%). After 30 min at -78 °C, the reaction mixture was poured into a sat. aq solution of NaHCO₃ and extracted with ether. The combined extracts were washed with brine, dried over MgSO₄, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (Cyclohexane/EtOAc: 90/10) to give 774 mg (91%) of 20 [18b] as a colorless oil.

  Article in Thieme Connect
• 18b Braga AL. Dornelles L. Silveira CC. Wessjohann LA. Synthesis  1999,  562 
  Article in Thieme ConnectGoogle Scholar
• 19a TMSNTf₂ was generated by protodesilylation of allyltrimethylsilane with TFSI-H: Mathieu B. Ghosez L. Tetrahedron Lett.  1997,  38:  5497 
  CrossrefGoogle Scholar
• 19b

  Protodesilylation of trimethylsilyl enol ethers could also generate TMSNTf₂, but at -78 °C, under the reaction conditions, the rate of this reaction was not checked.

  Crossref
• 20 Sakurai H. Pure Appl. Chem.  1982,  54:  1 
  CrossrefGoogle Scholar
• 21 Fleming I. Dunogues J. Smithers R. Org. React.  1989,  37:  57 
  Google Scholar
• 22 Schinzer D. Synlett  1988,  263 
  Google Scholar
• 23 Hosomi A. Sakurai H. Tetrahedron Lett.  1976,  1295 
  CrossrefGoogle Scholar
• 24 Calas R. Dunogues J. Deleris G. Pisciotti F. J. Organomet. Chem.  1974,  69:  C 15 
  Google Scholar
• 25 Hosomi A. Shirabata A. Sakurai H. Tetrahedron Lett.  1978,  3043 
  CrossrefGoogle Scholar
• 26 Chan TH. Fleming I. Synthesis  1979,  761 
  Article in Thieme ConnectGoogle Scholar
• 27 Lipshutz BH. Ellsworth EL. Dimock SH. Smith RAJ. J. Am. Chem. Soc.  1990,  112:  4404 
  CrossrefGoogle Scholar
• 28 Lipshutz BH. Hackmann C. J. Org. Chem.  1994,  59:  7437 
  CrossrefGoogle Scholar
• 29 Yanagisawa A. Habaue S. Yasue K. Yamamoto H. J. Am. Chem. Soc.  1994,  116:  6130 
  CrossrefGoogle Scholar
• 30 Hosomi A. Sakurai H. J. Am. Chem. Soc.  1977,  99:  1673 
  CrossrefGoogle Scholar
• 31 Kuhnert N. Peverley J. Robertson J. Tetrahedron Lett.  1998,  39:  3215 
  CrossrefGoogle Scholar
• 32 Narasaka K. Soai K. Mukaiyama T. Chem. Lett.  1974,  1223 
  CrossrefGoogle Scholar
• 33 Brownbridge P. Synthesis  1983,  1 
  Article in Thieme ConnectGoogle Scholar
• 34 Lohray BB. Zimbiniski R. Tetrahedron Lett.  1990,  31:  7273 
  CrossrefGoogle Scholar
• 35 Heathcock CH. Norman MH. Uehling DE. J. Am. Chem. Soc.  1985,  107:  2797 
  CrossrefGoogle Scholar
• 36 Ohki H. Wada M. Akiba K. Tetrahedron Lett.  1988,  19:  4719 
  Google Scholar
• 37 Duhamel P. Dujardin G. Hennequin L. Poirier J.-M. J. Chem. Soc., Perkin Trans.1  1992,  387 
  Google Scholar
• 38 Gray BD. White D. J. Chem. Soc., Chem. Commun.  1985,  20 
  CrossrefGoogle Scholar
• 39 Hagiwara H. Okano A. Akama T. Uda H. J. Chem. Soc., Chem. Commun.  1987,  1333 
  CrossrefGoogle Scholar
• 40 Mukaiyama T. Tamura M. Kobayashi S. Chem. Lett.  1986,  1817 
  Google Scholar
• 41 Yura T. Iwasawa N. Narasaka K. Mukaiyama T. Chem. Lett.  1988,  1025 
  Google Scholar
• 42 Sato T. Wakahara Y. Otera J. Nozaki H. Tetrahedron  1991,  47:  9773 
  CrossrefGoogle Scholar
• 43 Kobayashi S. Hachiya I. Ishitani H. Araki M. Synlett  1993,  472 
  Article in Thieme ConnectGoogle Scholar
• 44 Le Roux C. Gaspard-Iloughmane H. Dubac J. Jaud J. Vignaux P. J. Org. Chem.  1993,  58:  1835 
  CrossrefGoogle Scholar
• 45 Tanaka M. Suemune H. Sakai K. Tetrahedron Lett.  1988,  29:  1733 
  CrossrefGoogle Scholar
• 47 Ferrier RJ. Prasad N. J. Chem. Soc. C  1969,  570 
  CrossrefGoogle Scholar
• 48 Ferrier RJ. Adv. Carbohydr. Chem. Biochem.  1969,  24:  199 
  Google Scholar
• 49 Danishefsky SJ. DeNinno S. Lartey P. J. Am. Chem. Soc.  1987,  109:  2082 
  CrossrefGoogle Scholar
• 50 Danishefsky SJ. Selnick HG. Zelle RE. DeNinno MP. J. Am. Chem. Soc.  1988,  110:  4368 
  CrossrefGoogle Scholar
• 51 Danishefsky SJ. Armistead DM. Wincott FE. Selnick HG. Hungate R. J. Am. Chem. Soc.  1989,  111:  2967 
  CrossrefGoogle Scholar
• 52 Danishefsky SJ. Armistead DM. Wincott FE. Selnick HG. Hungate R. J. Am. Chem. Soc.  1987,  109:  8117 
  CrossrefGoogle Scholar
• 53 Danishefsky SJ. Selnick HG. Armistead DM. Wincott FE. J. Am. Chem. Soc.  1987,  109:  8119 
  CrossrefGoogle Scholar
• 54 Tsukiyama T. Isobe M. Tetrahedron Lett.  1992,  33:  7911 
  CrossrefGoogle Scholar

Determined by ¹H NMR.