Palladium(0)-Catalyzed Silylation of Aryl Halides with Triorganosilanes: Synthesis of Aryl(2-furyl)silanes

Abstract

Triorganosilanes, which possess two aryl groups on the silicon atom, undergo palladium-catalyzed silylation of aryl iodides. Aryl(2-furyl)silanes thus obtained are potentially useful starting materials for carbon-carbon bond-forming reactions in the presence of transition-metal catalysts and tetrabutylammonium fluo­ride.

silicon - palladium - catalysis - cross-coupling - halides

References

<A NAME="RF20205SS-1A">1a</A> Murata M. Watanabe S. Masuda Y. J. Org. Chem.  1997,  62:  6458 

<A NAME="RF20205SS-1B">1b</A> Murata M. Oyama T. Watanabe S. Masuda Y. J. Org. Chem.  2000,  65:  164 

<A NAME="RF20205SS-1C">1c</A> Baudoin O. Guénard D. Guéritte F. J. Org. Chem.  2000,  65:  9268 

<A NAME="RF20205SS-1D">1d</A> Broutin P.-E. Čerña I. Campaniello M. Leroux F. Colobert F. Org. Lett.  2004,  6:  4419 

<A NAME="RF20205SS-2A">2a</A> Murata M. Suzuki K. Watanabe S. Masuda Y. J. Org. Chem.  1997,  62:  8569 

<A NAME="RF20205SS-2B">2b</A> Manoso AS. DeShong P. J. Org. Chem.  2001,  66:  7455 

<A NAME="RF20205SS-2C">2c</A> Murata M. Ishikura M. Nagata M. Watanabe S. Masuda Y. Org. Lett.  2002,  4:  1843 

<A NAME="RF20205SS-2D">2d</A> Komuro K. Ishizaki K. Suzuki H. Touagousei-kenkyu-nenpo  2003,  6:  24 

<A NAME="RF20205SS-3">3</A> Nakamura T. Kinoshita H. Shinokubo H. Oshima K. Org. Lett.  2002,  4:  3165 

<A NAME="RF20205SS-4">4</A> Murata M. Watanabe S. Masuda Y. Synlett  2000,  1043 

<A NAME="RF20205SS-5A">5a</A> Murata M. Watanabe S. Masuda Y. Tetrahedron Lett.  1999,  40:  9255 

<A NAME="RF20205SS-5B">5b</A> Denmark SE. Kallemeyn JM. Org. Lett.  2003,  5:  3483 

<A NAME="RF20205SS-6">6</A> The silylation using trialkylsilanes was reported, however, no example of diarylmethylsilanes was provided, see: Yamanoi Y. J. Org. Chem.  2005,  70:  9607 

<A NAME="RF20205SS-7">7</A> The Chemistry of Organic Silicon Compounds   Patai S. Rappoport Z. Wiley & Sons; New York: 2000. 

For examples of coupling reactions of aryl nonaflates, see:

<A NAME="RF20205SS-8A">8a</A> Rottlander M. Knochel P. J. Org. Chem.  1998,  63:  203 

<A NAME="RF20205SS-8B">8b</A> Anderson KW. Mendez-Perez M. Priego J. Buchwald SL. J. Org. Chem.  2003,  68:  9563 

<A NAME="RF20205SS-9A">9a</A> Itami K. Nokami T. Yoshida J. J. Am. Chem. Soc.  2001,  123:  5600 

<A NAME="RF20205SS-9B">9b</A> Itami K. Nokami T. Ishimura Y. Mitsudo K. Kamei T. Yoshida J. J. Am. Chem. Soc.  2001,  123:  11577 

<A NAME="RF20205SS-10">10</A> Hosoi K. Nozaki K. Hiyama T. Chem. Lett.  2002,  138 

For examples of the cross-coupling reaction of other all-carbon-substituted organosilanes, see:

<A NAME="RF20205SS-11A">11a</A> Denmark SE. Choi JY. J. Am. Chem. Soc.  1999,  121:  5821 

<A NAME="RF20205SS-11B">11b</A> Nakao Y. Oda T. Sahoo AK. Hiyama T. J. Organomet. Chem.  2003,  687:  570 

<A NAME="RF20205SS-11C">11c</A> Trost BM. Machacek MR. Ball ZT. Org. Lett.  2003,  5:  1895 

<A NAME="RF20205SS-12">12</A>

Cross-coupling of aryltri(2-furyl)germanes with aryl halides has been reported, see ref. 3.

<A NAME="RF20205SS-13A">13a</A> Huang TS. Li CJ. Chem. Commun.  2001,  2348 

<A NAME="RF20205SS-13B">13b</A> Mori A. Danda Y. Fujii T. Hirabayashi K. Osakada K. J. Am. Chem. Soc.  2001,  123:  10774 

<A NAME="RF20205SS-13C">13c</A> Fujii T. Koike T. Mori A. Osakada K. Synlett  2002,  298 

<A NAME="RF20205SS-13D">13d</A> Koike T. Du X. Mori A. Osakada K. Synlett  2002,  301 

<A NAME="RF20205SS-13E">13e</A> Oi S. Honma Y. Inoue Y. Org. Lett.  2002,  4:  667 

<A NAME="RF20205SS-13F">13f</A> Murata M. Shimazaki R. Ishikura M. Watanabe S. Masuda Y. Synthesis  2002,  717 

<A NAME="RF20205SS-14">14</A>

To some extent a plausible mechanism can be derived from that proposed by us for triethoxysilane (see ref. 2a); however, the role of KI (Table [2] , entries 9-12) is not easily interpreted.

<A NAME="RF20205SS-15">15</A> Cunico RF. Bedell L. J. Org. Chem.  1980,  45:  4797