Cycloaddition of Zirconacyclopentadiene with 2-Bromoacrylate, 2-Bromoacrylaldehyde, and 3-Bromofuran-2,5-dione in the Presence of CuCl: A New Pathway for the Formation of Benzene Derivatives and Isobenzofuran-1,3-dione

REFERENCES

• Negishi , E. ; Cederbaum , F. E. ; Takahashi , T. Metal-promoted cyclization, 11: Reaction of zirconocene dichloride with alkyllithiums or alkyl Grignard reagents as a convenient method for generating a zirconocene equivalent and its use in zirconium-promoted cyclization of alkenes, alkynes, dienes, enynes, and diynes . Tetrahedron Lett. 1986 , 27 , 2829 – 2832 .
   Google Scholar
• Negishi , E. ; Holms , S. J. ; Your , J. ; Miller , J. A. ; Cederbaum , F. E. ; Swanson , D. R. ; Takahashi , T. Novel bicyclization of enynes and diynes promoted by zirconocene derivatives and conversion of zirconabicycles into bicyclic enones via carbonylation . J. Am. Chem. Soc. 1989 , 111 , 3336 – 3346 .
   Google Scholar
• Xi , Z. ; Hara , R. ; Takahashi , T. Highly selective and practical alkyne–alkyne cross-coupling using Cp2ZrBu2 and ethylene . J. Org. Chem. 1995 , 60 , 4444 – 4448 .
   Google Scholar
• Takahashi , T. ; Xi , Z. ; Rousset , C. J. ; Suzuki , N. Pair-selective coupling of alkynes with alkenes on zirconocene complex . Chem. Lett. 1993 , 1001 – 1004 .
   Google Scholar
• Buchwald , S. L. ; Watson , B. T. ; Huffman , J. C. Elective, zirconium-mediated cross-coupling of alkynes: The synthesis of isomerically pure 1,3-dienes and 1,4-diiodo-1,3-dienes . J. Am. Chem. Soc. 1987 , 111 , 2870 – 2874 .
   Google Scholar
• Takahashi , T. ; Swanson , D. R. ; Negishi , E. Zirconacyclopropanes and zirconacyclopropenes: Synthesis, characterization, and reactions . Chem. Lett. 1987 , 623 – 626 .
   Google Scholar
• Takahashi , T. ; Li , Y. Zirconacyclopentadienes in organic synthesis . In Titanium and Zirconium in Organic Synthesis , I. Marek (Ed.); Wiley-VCH Verlag : Weinheim , Germany , 2002 ; chap 2 .
   Google Scholar
• Negishi , E. Organozirconium chemistry in organic synthesis . In Organometallics in Synthesis, , 2nd ed. ; M. Schlosser (Ed.); Wiley : New York , 2002 ; chap 8 .
   Google Scholar
• Takahashi , T. ; Kotora , M. ; Xi , Z. Cycloaddition of zirconacyclopentadienes to alkynes using copper salts: Formation of benzene derivatives . J. Chem. Soc., Chem. Commun. 1995 , 361 – 362 .
   Google Scholar
• Takahashi , T. ; Xi , Z. ; Yamazaki , A. ; Liu , Y. ; Nakajima , K. ; Kotora , M. Cycloaddition reaction of zirconacyclopentadienes to alkynes: Highly selective formation of benzene derivatives from three different alkynes . J. Am. Chem. Soc. 1998 , 120 , 1672 – 1680 .
   Google Scholar
• Takahashi , T. ; Tsai , F.-Y. ; Kotora , M. Selective formation of substituted pyridines from two different alkynes and a nitrile: Novel coupling reaction of azazirconacyclopentadienes with alkynes . J. Am. Chem. Soc. 2000 , 122 , 4994 – 4995 .
   Google Scholar
• Kotora , M. ; Xi , C. ; Takahashi , T. Cross-coupling–conjugate addition reaction of zirconacyclopentadienes with 3-iodopropenoates . Tetrahedron Lett. 1998 , 39 , 4321 – 4324 .
   Google Scholar
• Xi , C. ; Kotora , M. ; Nakajima , K. ; Takahashi , T. Reaction of zirconacycles with 3-iodopropenoates and 3-iodocycloenones in the presence of CuCl: A new pathway for the formation of cyclopentadienes and spirocyclic compounds . J. Org. Chem. 2000 , 65 , 945 – 950 .
   Google Scholar
• For representative examples of the transmetallation of zirconacyclopentadienes to CuCl, see Takahashi , T. ; Kotora , M. ; Kasai , K. ; Suzuki , N. Novel syntheses of eight-membered–five-membered fused-ring compounds from zirconacyclopentadienes . Organometallics 1994 , 13 , 4183 – 4185 .
   Google Scholar
• Wovkulich , P. M. ; Uskokovic , M. R. Direct α-iodination of cycloalkenones . Tetrahedron Lett. 1992 , 33 , 917 – 918 .
   Google Scholar
• Rachon , J. ; Goedken , V. ; Walborsky , H. M. Rearrangement of a bicyclic [2.2.2] system to a bicyclic [3.2.1] system: Nonclassical ions . J. Org. Chem. 1989 , 54 , 1006 – 1012 .
   Web of Science ®Google Scholar