Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 12
1,084
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

New Methodology for the Synthesis of α,α-difluoroketones

Pages 1940-1945 | Received 17 Jan 2008, Published online: 12 Jun 2008

REFERENCES

  • (a) Isanbor , C. ; O'Hagan , D. Fluorine in medicinal chemistry: A review of anticancer agents . J. Fluorine Chem. 2006 , 127 , 303 – 319 ; (b) Ismail , F. Important fluorinated drugs in experimental and clinical use . J. Fluorine Chem. 2002 , 118 , 27 – 33 ; (c) Park , B. K. ; Kitteringham , N. R. ; O'Neill , P. M. Metabolism of fluorine containing drugs . Ann. Rev. Pharmacol. Toxicol. 2001 , 41 , 443 – 470 ; (d) Reiss , J. G. Fluorine in our arteries . New J. Chem. 1995 , 19 , 891 – 909 ; (e) Park , B. K. ; Kitteringham , N. R. Effects of fluorine on drug metabolism . Drug Metabolism Rev. 1994 , 26 , 605 – 643 ; (f) Shengguo , S. ; Adeboye , A. Fluorinated molecules as drugs and imaging agents in the CNS . Curr. Top Med. Chem. 2006 , 6 , 1457 – 1464 ; (g) Kirk , K. L. Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules . J. Fluorine Chem. 2006 , 127 , 1013 – 1029 .
  • Dicciani , N. K. Fluorine. Chem. Engin. News 2003, 58, 48.
  • (a) Dwyer , M. P. ; Yu , Y. ; Chao , J. ; Aki , C. ; Chao , J. ; Biju , P. ; Girijavallabhan , V. ; Rindgen , D. ; Bond , R. ; Mayor-Ezel , R. ; Jakway , J. ; Hipkin , R. W. ; Fossetta , J. ; Gonsiorek , W. ; Bian , H. ; Fan , X. ; Terminelli , C. ; Fine , J. ; Lundell , D. ; Merritt , J. R. ; Rokoz , L. L. ; Kaiser , B. ; Li , G. ; Wang , W. ; Stauffer , T. ; Ozgur , L. ; Baldwin , J. ; Taveras , A. G. Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): A potent, orally bioavailable CXCR2/CXCR1 receptor antagonist . J. Med. Chem. 2006 , 49 , 7603 – 7606 ; (b) Widdowson , K. L. ; Elliot , J. D. ; Veber , D. F. ; Nie , H. ; Rutledge , M. C. ; McCleland , B. W. ; Xiang , J.-N. ; Jurewicz , A. ; White , J. R. ; Sarau , H. M. Evaluation of potent and selective small molecule antagonist for the CXCR2 chemokine receptor . J. Med. Chem. 2004 , 47 , 1319 – 1321 .
  • Hill , B. ; Liu , Y. ; Taylor , S. D. Synthesis of α-fluorosulfonamides by electrophilic fluorination . Org. Lett. 2004 , 6 , 4285 – 4288 , and references cited therein .
  • Fritz-Lanhals , E. Synthesis of optically active (2-fluoroacyl) benzenes . Synlett 1999 , 11 , 1805 – 1807 .
  • (a) Ayuba , S. ; Yoneda , N. ; Fukuhara , T. ; Hara , S. Fluorination of sulfides using IF5-Et3N.3HF . Bull. Chem. Soc. Jpn. 2002 , 75 , 1597 – 1604 ; (b) Stavber , G. ; Zupan , M. ; Jereb , M. ; Stavber , S. Selective and effective fluorination of organic compounds in water using selectfluor F-TEDA-BF4 . Org. Lett. 2004 , 6 , 4973 – 4976 ; (c) Ridge , D. N. ; Hanifin , J. W. ; Harten , L. A. ; Johnson , B. D. ; Menschick , J. ; Nicolau , G. ; Sloboda , A. E. ; Watts , D. E. Potential antiarthritic agents, 2: Benzoylacetonitriles and β-amino cinnamonitrile . J. Med. Chem. 1979 , 22 , 1385 – 1389 .
  • (a) Koch , G. ; Loiseleur , O. ; Altmann , K. H. Total synthesis of 26-fluoro-epothilone B . Synlett 2004 , 4 , 693 – 697 ; (b) Golubev , A. S. ; Schedel , H. ; Radics , G. ; Fioroni , M. ; Thust , S. ; Burger , K. Hexafluoroacetone as a protecting and activating reagent 5,5-difluoro- and trans-5-fluoropipecolic acids from glutamic acid . Tetrahedron Lett. 2004 , 45 , 1445 – 1447 ; (c) Singh , R. P. ; Shreeve , J. M. Recent advances in nucleophilic fluorination reactions of organic compounds with Deoxofluor and DAST . Synthesis 2002 , 17 , 2561 – 2578 .
  • Jen , K. Y. ; Cava , M. P. Improved synthesis of aromatic diselenides . J. Org. Chem. 1983 , 48 , 1449 – 1451 .
  • (a) Chadwick , D. J. ; Chambers , J. ; Hargraves , H. E. ; Meakins , G. D. ; Snowden , R L. Preparation of substituted furan- and thiophene-2-carboxaldehydes and -2-[2H]carboxaldehydes, and of 2-furyl ketones . J. Chem. Soc., Perkin Trans. 1973 , 20 , 2327 – 2332 ; (b) Gilman , H. ; Calloway , N. O. ; Burtner , R. R. Orientation in the furan series, IX: The Friedel–Crafts reaction with 2-furfural . J. Am. Chem. Soc. 1935 , 57 , 906 – 907 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.