Electrophilic Fluorination of a Highly Functionalized Pyrrole

References

• Schlosser , M. 1978 . Tetrahedron , 34 : 3
   Web of Science ®Google Scholar
• Filler , R. and Kobayashi , Y. 1986 . Biochemical Aspects of Fluorine Chemistry , New York, N. Y. : Elsevier Biomedical Press .
   Google Scholar
• Kuhn , D. G. , Kamhi , V. M. , Furch , J. A. , Diehl , R. E. , Trotto , S. H. , Lowen , G. T. and Babcock , J. T. 1992 . Synthesis and Chemistry of Agrochemicals III , ACS Symposium Series 504 Edited by: Baker , D. R. , Fenyes , J. S. and Steffens , J. J. 298 – 305 . Washington, DC : American Chemical Society .
   Google Scholar
• Brown , D. G. , Siddens , J. K. , Diehl , R. E. and Wright , D. P. U.S. Patent 5,010,048 . 1991 .
   Google Scholar
• Chang , M. N. , Biftu , T. , Boulton , D. A. , Finke , R. E. , Hammond , M. L. , Pessolano , A. A. , Zambias , R. A. , Bailey , P. , Goldenberg , M and Rackham , A. 1986 . Eur. J. Med. Chem.-Chem. Ther. , 21 : 363
   Web of Science ®Google Scholar
• Onda , H. , Toi , H. , Aoyama , Y. and Ogoshi , H. 1985 . Tetrahedron Lett. , 26 : 4221
   Google Scholar
• Differding , E. and Ofner , H. 1991 . Synlett , : 187
   Google Scholar
• Bray , B. L. , Mathies , P. H. , Naef , R. , Solas , D. R. , Tidwell , T. T. , Artis , D. R. and Muchowski , J. M. 1990 . J. Org. Chem. , 55 : 6317
   Web of Science ®Google Scholar
• Treatment of 7 with methyl iodide affords 3-methyl-1-(triisopropyl silyl)pyrrole in greater than 90% yield as described in reference 6.
   Google Scholar
• Differding , E. and Rüegg , G. A. 1991 . Tetrahedron Lett. , 32 : 3815
   Google Scholar
• Differding , E. and Wehrli , M. 1991 . Tetrahedron Lett. , 32 : 3819
   Google Scholar
• Differding , E. and Bersier , P. M. 1992 . Tetrahedron , 48 : 1595
   Google Scholar
• Generation of 10 could be achieved by treatment of 1 with n-BuLi (1.2 eq) or t-BuLi (2.1 eq). However with n-BuLi, a small amount of butylated material derived from the reaction of 10 with n-BuBr was detected.
   Google Scholar
• Meek , J. and Stockton , G. U. S. Patent 4 686 365 . 1987 .
   Google Scholar
• N-fluorbenzenesulfonimide was provided by Allied-Signal Inc.
   Google Scholar
• Identical to 1-(triisopropylsilyl)pyrrole, described in reference 6.
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• Identical to 2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifuluoro methyl)pyrrole-3-carbonitrie, described in reference 2b.
   Google Scholar