Hydrostannation of Diyne and Triyne π-Electron Bridges: Efficient Stille Cross-Coupling of 1,3,5-Tris[(E)-2-(tributylstannyl)vinyl]benzene

Abstract

The facile hydrostannation of diynes and triynes with tributyltin hydride was achieved. The hydrostannation product readily underwent the Stille cross-coupling reaction with a variety of aryl bromides. The copper-mediated Stille cross-coupling of 1,3,5-tris[(E)-2-(tributylstannyl)vinyl]benzene with (E)-β-iodostyrene afforded the conjugated diene.

hydrostannation - Stille cross-coupling - 1,3,5-triethynylbenzene - diethynylsubstrate - trans-tributyltinvinyl compound

References

<A NAME="RF15704SS-1A">1a</A> Pereyre M. Quintard JP. Rahm A. Tin in Organic Synthesis   Butterworth; London: 1987. 

<A NAME="RF15704SS-1B">1b</A> Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 

<A NAME="RF15704SS-2A">2a</A> Nativi C. Taddei M. J. Org. Chem.  1988,  53:  820 

<A NAME="RF15704SS-2B">2b</A> Corey EJ. Wollenberg RH. J. Org. Chem.  1975,  40:  2265 

<A NAME="RF15704SS-2C">2c</A> Thiele CM. Mitchell TN. Eur. J. Org. Chem.  2004,  337 

<A NAME="RF15704SS-2D">2d</A> Nozaki K. Oshima K. Utimoto K. J. Am. Chem. Soc.  1987,  109:  2547 

<A NAME="RF15704SS-3A">3a</A> Rubina M. Rubin M. Gevorgyan V. J. Am. Chem. Soc.  2002,  124:  11566 

<A NAME="RF15704SS-3B">3b</A> Braune S. Pohlman M. Kazmaier U. J. Org. Chem.  2004,  69:  468 

<A NAME="RF15704SS-3C">3c</A> Zhang HX. Guibé F. Balavoine G. Tetrahedron Lett.  1988,  29:  619 

<A NAME="RF15704SS-3D">3d</A> Zhang HX. Guibé F. Balavoine G. J. Org. Chem.  1990,  55:  1857 

<A NAME="RF15704SS-3E">3e</A> Maleczka RE. Terstiege I. J. Org. Chem.  1998,  63:  9622 

<A NAME="RF15704SS-4">4</A> Leusink AJ. Budding HA. Drenth W. J. Organomet. Chem.  1967,  9:  295 

<A NAME="RF15704SS-5A">5a</A> Wang MS. Li ZH. Shek MF. Chow KH. Tao Y. D’Iorio M. J. Mater. Chem.  2000,  10:  1805 

<A NAME="RF15704SS-5B">5b</A> Van Hutten PF. Kransnikov VV. Hadziioannou G. Acc. Chem. Res.  1999,  32:  257 

<A NAME="RF15704SS-6A">6a</A> Tour JM. Acc. Chem. Res.  2000,  33:  791 

<A NAME="RF15704SS-6B">6b</A> Yamamoto T. Macromol. Rapid Commun.  2002,  23:  583 

<A NAME="RF15704SS-7">7</A> Smith ND. Mancuso J. Lautens M. Chem. Rev.  2000,  100:  3257 

<A NAME="RF15704SS-8A">8a</A> Crisp GT. Gebauer MG. J. Organomet. Chem.  1997,  532:  83 

<A NAME="RF15704SS-8B">8b</A> Leusink AJ. Budding HA. Marsman JW. J. Organomet. Chem.  1967,  9:  285 

<A NAME="RF15704SS-9">9</A> Rim C. Son DY. Org. Lett.  2003,  5:  3443 

<A NAME="RF15704SS-10">10</A> Farina V. Roth GP. Advances in Metal-Organic Chemistry   Vol. 5:  Liebeskind LS. JAI Press; Greenwich: 1996.  p.91 

<A NAME="RF15704SS-11">11</A> Maleczka RE. Terrell LR. Clark DH. Whitehead SL. Gallagher WP. Terstiege I. J. Org. Chem.  1999,  64:  5958 

<A NAME="RF15704SS-12">12</A> Farina V. Krishnan B. J. Am. Chem. Soc.  1991,  113:  9585 

<A NAME="RF15704SS-13A">13a</A> Fujita M. Oka H. Ogura K. Tetrahedron Lett.  1995,  36:  5247 

<A NAME="RF15704SS-13B">13b</A> Tsuji Y. Kajita S. Isobe S. Funato M. J. Org. Chem.  1993,  58:  3607 

<A NAME="RF15704SS-13C">13c</A> Farina V. Krishnan B. Marshall DR. Roth GP. J. Org. Chem.  1993,  58:  5434 

<A NAME="RF15704SS-14">14</A> Mee SPH. Lee V. Baldwin JE. Angew. Chem. Int. Ed.  2004,  43:  1132 

<A NAME="RF15704SS-15A">15a</A> Allred GD. Liebeskind LS. J. Am. Chem. Soc.  1996,  118:  2748 

<A NAME="RF15704SS-15B">15b</A> Farina V. Kapadia S. Krishnan B. Wang C. Liebeskind LS. J. Org. Chem.  1994,  59:  5905 

<A NAME="RF15704SS-15C">15c</A> Roht GP. Farina V. Liebeskind LS. Peña-Cabrera E. Tetrahedron Lett.  1995,  36:  2191 

<A NAME="RF15704SS-15D">15d</A> Barchin BM. Valenciano J. Cuadro AM. Alvarez-Builla J. Vaquero J. Org. Lett.  1999,  1:  545 

<A NAME="RF15704SS-16A">16a</A> Gallagher WP. Terstiege I. Maleczka RE. J. Am. Chem. Soc.  2001,  123:  3194 

<A NAME="RF15704SS-16B">16b</A> Stille JK. Groh BL. J. Am. Chem. Soc.  1987,  109:  813 

<A NAME="RF15704SS-17">17</A> Takahashi S. Kuroyama Y. Sonogashira K. Hagihara N. Synthesis  1980,  627 

<A NAME="RF15704SS-18">18</A> Leininger S. Stang PJ. Huang S. Organometallics  1998,  17:  3981 

<A NAME="RF15704SS-19">19</A> Thomas KRJ. Lin JT. Lin Y.-Y. Tsai C. Sun S.-S. Organometallics  2001,  20:  2262 

<A NAME="RF15704SS-20">20</A> Beginn C. Gar˛ulevičius JV. Strohriegl P. Simmerer J. Haarer D. Macromol. Chem. Phys.  1994,  195:  2353 

<A NAME="RF15704SS-21">21</A> Pei J. Ni J. Zhou X.-H. Cao X.-Y. Lai Y.-H. J. Org. Chem.  2002,  67:  4924 

<A NAME="RF15704SS-22">22</A> Fabian KHH. Elwahy AHM. Hafner K. Tetrahedron Lett.  2000,  41:  2855 

<A NAME="RF15704SS-23">23</A> Lee DW. Kwon K.-Y. Jin J.-I. Park Y. Kim Y.-R. Hwang I.-W. Chem. Mater.  2001,  13:  565