Improved Procedure for Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl Halides with Aryltrimethoxysilanes under Solvent-Free Conditions

Abstract

An improved palladium-catalyzed Hiyama cross-coupling reaction is reported. In the presence of PdCl₂(MeCN)₂, P(o-tol)₃ and TBAF, a number of ArX (X = I, Br, Cl) were coupled with ArSi(OMe)₃ efficiently to afford the desired cross-coupled products in moderate to excellent yields. It is noteworthy that this protocol is conducted under relatively low Pd loadings and solvent-free conditions.

PdCl₂(MeCN)₂ - Hiyama cross-coupling reaction - aryl halide - arylsiloxane

References

<A NAME="RF15005SS-1">1</A> Bringmann G. Gunther C. Ochse M. Schupp O. Tasler S. Progress in the Chemistry of Organic Natural Products   Vol. 82:  Herz W. Falk H. Kirby GW. Moore RE. Springer; Berlin: 2001.  p.1-293  

<A NAME="RF15005SS-2">2</A> Hegedus LS. Organometallics in Synthesis   Schlosser M. Wiley; Chichester: 2002.  p.1123 

For selected Ullmann coupling reactions, see:

<A NAME="RF15005SS-3A">3a</A> Brongmann G. Walter R. Weirich R. Angew. Chem., Int. Ed. Engl.  1990,  29:  977 

<A NAME="RF15005SS-3B">3b</A> Zhang S. Zhang D. Liebeskind LS. J. Org. Chem.  1997,  62:  2312 

<A NAME="RF15005SS-3C">3c</A> Li J.-H. Xie Y.-X. Yin D.-L. J. Org. Chem.  2003,  68:  9867 ; and references cited therein

For selected reviews on the Hiyama cross-coupling reaction, see:

<A NAME="RF15005SS-4A">4a</A> Diederich F. Stang PJ. Metal-Catalyzed Cross-Coupling Reactions   Wiley-VCH; Weinheim: 1998. 

<A NAME="RF15005SS-4B">4b</A> Miyaura N. Cross-Coupling Reaction   Springer; Berlin: 2002. 

<A NAME="RF15005SS-4C">4c</A> Chuit C. Corriu RJP. Reye C. Young JC. Chem. Rev.  1993,  93:  1317 

<A NAME="RF15005SS-4D">4d</A> Horn KA. Chem. Rev.  1995,  95:  1317 

For selected papers on palladium-phosphine catalytic systems for the Hiyama cross-coupling reaction of siloxanes, see:

<A NAME="RF15005SS-5A">5a</A> Mowery ME. DeShong P. Org. Lett.  1999,  1:  2137 

<A NAME="RF15005SS-5B">5b</A> Mowery ME. DeShong P. J. Org. Chem.  1999,  64:  1684 

<A NAME="RF15005SS-5C">5c</A> McElroy WT. DeShong P. Org. Lett.  2003,  5:  4779 

<A NAME="RF15005SS-5D">5d</A> Lee J.-Y. Fu GC. J. Am. Chem. Soc.  2003,  125:  5616 

<A NAME="RF15005SS-5E">5e</A> Koike T. Mori A. Synlett  2003,  1850 

<A NAME="RF15005SS-5F">5f</A> Wolf C. Lerebours R. Org. Lett.  2004,  6:  1147 

<A NAME="RF15005SS-5G">5g</A> Seganish WM. DeShong P. J. Org. Chem.  2004,  69:  1137 

<A NAME="RF15005SS-5H">5h</A> Lerebours R. Wolf C. Synthesis  2005,  2287 

For selected papers on palladium-phosphine catalytic systems for the Hiyama cross-coupling reaction of other silanes, see:

<A NAME="RF15005SS-6A">6a</A> Hatanaka Y. Fukushima S. Hiyama T. Chem. Lett.  1989,  1711 

<A NAME="RF15005SS-6B">6b</A> Hatanaka Y. Gouda Y. Okahara T. Hiyama T. Tetrahedron  1994,  50:  8301 

<A NAME="RF15005SS-6C">6c</A> Gouda K. Hagiwara E. Hatanaka Y. Hiyama T. J. Org. Chem.  1996,  61:  7232 

<A NAME="RF15005SS-6D">6d</A> Hagiwara E. Gouda K. Hatanaka Y. Hiyama T. Tetrahedron Lett.  1997,  38:  439 

<A NAME="RF15005SS-6E">6e</A> Denmark SC. Choi JU. J. Am. Chem. Soc.  1999,  121:  5821 

<A NAME="RF15005SS-6F">6f</A> Mowery ME. DeShong P. J. Org. Chem.  1999,  64:  3266 ; and references cited therein

<A NAME="RF15005SS-6G">6g</A> Hirabayashi K. Kawashima J. Nishihara Y. Mori A. Hiyama T. Org. Lett.  1999,  1:  299 

<A NAME="RF15005SS-6H">6h</A> Denmark SC. Wu Z. Org. Lett.  1999,  1:  1495 

<A NAME="RF15005SS-6I">6i</A> Hirabayashi K. Mori A. Kawashima J. Suguro M. Nishihara Y. Hiyama T. J. Org. Chem.  2000,  65:  5342 

<A NAME="RF15005SS-6J">6j</A> Mori A. Suguro M. Synlett  2001,  845 

<A NAME="RF15005SS-6K">6k</A> Hoosoi K. Nozaki K. Hiyama T. Chem. Lett.  2002,  138 

<A NAME="RF15005SS-6L">6l</A> Nakao Y. Oda T. Sahoo AK. Hiyama T. J. Organomet. Chem.  2003,  687:  570 

<A NAME="RF15005SS-6M">6m</A> Sahoo AK. Oda T. Nakao Y. Hiyama T. Adv. Synth. Catal.  2004,  346:  1715 

<A NAME="RF15005SS-6N">6n</A> Pierrat P. Gros P. Fort Y. Org. Lett.  2005,  7:  697 

<A NAME="RF15005SS-6O">6o</A> Jayanth TT. Jeganmohan M. Cheng C.-H. Org. Lett.  2005,  7:  2921 

<A NAME="RF15005SS-6P">6p</A> Shindo M. Matsumoto K. Shishido K. Synlett  2005,  176 

<A NAME="RF15005SS-6Q">6q</A> Nakao Y. Imanaka H. Sahoo AK. Yada A. Hiyama T. J. Am. Chem. Soc.  2005,  127:  6952 

<A NAME="RF15005SS-7">7</A> For a papers on palladium-imidazolium chloride catalytic system for the Hiyama cross-coupling reaction, see: Lee HM. Nolan SP. Org. Lett.  2000,  2:  2053 

<A NAME="RF15005SS-8">8</A> For a papers on β-diimine-palladium catalysts for the Hiyama cross-coupling reaction, see: Domin D. Benito-Garagorri D. Mereiter K. Fröhlich J. Kirchner K. Organometallics  2005,  24:  3957 

For papers on DABCO as a ligand for the palladium-catalyzed cross-coupling reactions, see:

<A NAME="RF15005SS-9A">9a</A> Li J.-H. Liu W.-J. Org. Lett.  2004,  6:  2809 

<A NAME="RF15005SS-9B">9b</A> Li J.-H. Zhang X.-D. Xie Y.-X. Synthesis  2005,  804 

<A NAME="RF15005SS-9C">9c</A> Li J.-H. Liang Y. Wang D.-P. Liu W.-J. Xie Y.-X. Yin D.-L. J. Org. Chem.  2005,  70:  2832 

<A NAME="RF15005SS-10">10</A>

Only Pd(OAc)₂ as the Pd source was examined in reference 5a. We also attempted to reuse the PdCl₂(MeCN)₂/P(o-tol)₃/TBAF system, however, only a 48% yield of 3 was isolated in the second run.

<A NAME="RF15005SS-11">11</A> Akiyama R. Kobayashi S. Angew. Chem. Int. Ed.  2001,  40:  3469