Novel introduction of a tetrafluoroethylene (-CF2CF 2-) unit into organic molecules

Synthesis

Volumn , Issue 1, 2011, Pages 33-44

  Konno, Tsutomu ^a   Takano, Shinya ^a   Takahashi, Yoshikazu ^a   Konishi, Hideaki ^a   Tanaka, Yusuke ^a   Ishihara, Takashi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

MeLi LiBr free; reductive coupling; tetrafluoroethylene; triethyl(1,1,2,2 tetrafluorobut 3 enyl) silane

Indexed keywords

CARBONYL COMPOUNDS; HIGH YIELD; MELI/LIBR-FREE; ORGANIC MOLECULES; REDUCTIVE COUPLINGS; TETRABUTYLAMMONIUM FLUORIDES; TETRAFLUOROETHYLENE; TRIETHYL(1,1,2,2-TETRAFLUOROBUT-3-ENYL) SILANE;

ALDEHYDES; CARBONYLATION; MAGNESIUM;

FLUORINE CONTAINING POLYMERS;

1 (1,1,2,2 TETRAFLUOROBUT 3 ENYL)CYCLOHEXANOL; 1 (4 CHLOROPHENYL) 2,2,3,3 TETRAFLUOROPENT 4 EN 1 OL; 1 (4 CYANOPHENYL) 2,2,3,3 TETRAFLUOROPENT 4 EN 1 OL; 1 CYCLOHEXYL 2,2,3,3 TETRAFLUOROPENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (2 METHOXYPHENYL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (3 METHOXYPHENYL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (4 METHOXYPHENYL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (4 METHYLPHENYL) 4 PHENYLBUTANE 1,4 DIOL; 2,2,3,3 TETRAFLUORO 1 (4 METHYLPHENYL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (4 NITROPHENYL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 (FURAN 2 YL)PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 [4 (TRIFLUOROMETHYL)PHENYL]PENT 4 EN 1 OL; 2,2,3,3 TETRAFLUORO 1 PHENYLHEXANE 1,4 DIOL; 2,2,3,3 TETRAFLUORO 1 PHENYLPENT 4 EN 1 OL; 3,3,4,4 TETRAFLUORO 5 PHENYLTETRAHYDROFURAN 2 OL; 3,3,4,4 TETRAFLUOROHEPT 6 EN 3 OL; 3,3,4,4 TETRAFLUOROUNDEC 1 EN 5 OL; 3,3,4,5 TETRAFLUORO 2 (4 NITROPHENYL)HEX 5 EN 2 OL; 3,3,4,5 TETRAFLUORO 2 PHENYLHEX 5 EN 2 OL; 4,4,5,5 TETRAFLUORO 1 PHENYLHEPTA 1,6 DIEN 3 OL; 4,4,5,5 TETRAFLUORO 2,2 DIMETHYLHEPT 6 EN 3 OL; 5 ETHYL 3,3,4,4 TETRAFLUOROTETRAHYDROFURAN 1 OL; N (2,2,3,4 TETRAFLUORO 1 PHENYLPENT 4 ENYL) 2 METHYLPROPANE 2 SULFINAMIDE; N BENZYL 2,2,3,3 TETRAFLUORO 1 PHENYLPENT 4 ENYLAMINE; SILANE DERIVATIVE; TETRAFLUOROETHYLENE; TRIETHYL (1,1,2,2 TETRAFLUOROBUT 3 ENYL)SILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; ELECTROPHILICITY; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; HYDROPHOBICITY; NUCLEOPHILICITY; REACTION TIME; SYNTHESIS;

EID: 78650520626     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258330     Document Type: Article

References (24)

1. Purser S, Moore P R., Swallow S, Gouverneur V, Chem. Soc. Rev. 2008 37 320
2. O'Hagan D, Chem. Soc. Rev. 2008 37 308
3. Müller K, Faeh C, Diederich F, Science 2007 317 1881
4. Kirk K L., J. Fluorine Chem. 2006 127 1013
5. Bégué J P., Bonnet-Delpon D, J. Fluorine Chem. 2006 127 992
6. Isanbor C, O'Hagan D, J. Fluorine Chem. 2006 127 303
7. O'Hagen D, Rzepa H, Chem. Commun. 1997 645
8. Biomedical Frontiers of Fluorine Chemistry Ojima I McCarthy J R. Welch J T. American Chemical Society Washington DC 1996
9. Mann J, Chem. Soc. Rev. 1987 16 381
10. Welch J T., Tetrahedron 1987 43 3123
11. Uno H, Okada S, Ono T, Shiraishi Y, Suzuki H, J. Org. Chem. 1992 57 1504
12. Uneyama K, Kitagawa K, Tetrahedron Lett. 1991 32 375
13. Uneyama K, Kitagawa K, Tetrahedron Lett. 1991 32 3385
14. Gassman P G., O'Reilly N J., J. Org. Chem. 1987 52 2481
15. Biffinger J C., Kim H W., DiMagno S G., ChemBioChem 2004 5 622
16. Kim H W., Rossi P, Shoemaker R K., DiMagno S G., J. Am. Chem. Soc. 1998 120 9082
17. Timofte R S., Linclau B, Org. Lett. 2008 10 3673
18. Boydell A J., Vinader V, Linclau B, Angew. Chem. Int. Ed. 2004 43 5677
19. Bonnac L, Lee S E., Giuffredi G T., Elphick L M., Anderson A A., Child E S., Mann D J., Gouverneur V, Org. Biomol. Chem. 2010 8 1445
20. The absolute stereochemistry was determined on the basis of the stereochemical outcome in the reaction of the chiral sulfinimines with various organometallics. See:, Li Y, Ni C, Liu J, Zhang L, Zheng J, Zhu L, Hu J, Org. Lett. 2006 8 1693
21. Liu G, Cogan D A., Ellman J A., J. Am. Chem. Soc. 1997 119 9913
22. Prakash G K. S., Yudin A K., Chem. Rev. 1997 97 757
23. Singh R P., Shreeve J M., Tetrahedron 2000 56 7613
24. There has been no report on the synthesis of unsymmetric 2,2,3,3-tetrafluoro-1,4-diol derivatives. Two references, in which symmetric 2,2,3,3-tetrafluoro-1,4-diol derivatives were synthesized, have been published thus far., Fuchigami T, Hagiwara T, JP 6228030 1994, Dormidontov Y P., Shadrina L P., Zh. Org. Khim. 1983 19 269