A Convenient Iron-Catalyzed Method for the Preparation of 1,2-Bis(trimethylsilyl)benzenes

Abstract

A convenient iron-catalyzed method for the preparation of 1,2-bis(trimethylsilyl)benzenes is presented. Compared to the current procedures, low temperatures and toxic solvents are avoided, allowing large-scale preparation. Additionally, a variety of substituents are tolerated.

Grignard reaction - catalysis - iron - silicon - metalation

References

For selected examples with boron, see:

<A NAME="RT04910SS-1A">1a</A> Kaufmann D. Chem. Ber.  1987,  120:  853 

<A NAME="RT04910SS-1B">1b</A> With germanium, see: Zhun VI. Sbitneva IV. Polivanov AN. Chernyshev EA. Russ. J. Gen. Chem.  2006,  76:  1564 

<A NAME="RT04910SS-1C">1c</A> With palladium, see: Steenwinkel P. Gossage RA. Maunula T. Grove DM. van Koten G. Chem. Eur. J.  1998,  4:  763 

<A NAME="RT04910SS-1D">1d</A> With silver, see: Tyrra WE. J. Fluorine Chem.  2001,  112:  149 

<A NAME="RT04910SS-1E">1e</A> With indium, see: Choi ZH. Tyrra W. Adam A. Z. Anorg. Allg. Chem.  1999,  625:  1287 

<A NAME="RT04910SS-1F">1f</A> With mercury, see: Naumann D. Schulz F. Z. Anorg. Allg. Chem.  2005,  631:  122 

<A NAME="RT04910SS-2">2</A> For an example, see: Häbich D. Effenberger F. Synthesis  1979,  841 

<A NAME="RT04910SS-3">3</A> For an example, see: Sakurai H. Hosomi A. Kumada M. Tetrahedron Lett.  1969,  10:  1755 

<A NAME="RT04910SS-4">4</A> For an examples, see: Shippey MA. Dervan PB. J. Org. Chem.  1977,  42:  2654 

<A NAME="RT04910SS-5">5</A> For examples, see: Matsumoto H. Nagashima S. Yoshihiro K. Nagai Y. J. Organomet. Chem.  1975,  85:  C1 

For examples, see:

<A NAME="RT04910SS-6A">6a</A> Katz HE. J. Org. Chem.  1985,  50:  5027 

<A NAME="RT04910SS-6B">6b</A> Hilt G. Janikowski J. Hess W. Angew. Chem. Int. Ed.  2006,  45:  5204 

For examples, see:

<A NAME="RT04910SS-7A">7a</A> Tuulmets A. Ploom A. Panov D. Järv J. Synthesis  2010,  291 

<A NAME="RT04910SS-7B">7b</A> Effenberger F. Liebigs Ann. Chem.  1979,  842 

<A NAME="RT04910SS-8A">8a</A> Gilman H. Gaj BJ. J. Org. Chem.  1957,  22:  447 

<A NAME="RT04910SS-8B">8b</A> Leroux F. Schlosser M. Angew. Chem. Int. Ed.  2002,  41:  4272 

<A NAME="RT04910SS-8C">8c</A> Chen LS. Chen GJ. Tamborski C.
J. Organomet. Chem.  1980,  193:  283 

<A NAME="RT04910SS-9">9</A> Bettinger HF. Filthaus M. J. Org. Chem.  2007,  72:  9750 

<A NAME="RT04910SS-10">10</A> Kitamura T. Todaka M. Fujiwara Y. Org. Synth., Coll. Vol. X  , 

<A NAME="RT04910SS-11">11</A> Tilstam U. Weinmann H. Org. Process Res. Dev.  2002,  6:  906 

<A NAME="RT04910SS-12">12</A> Bogdanovic B. Schwickardi M. Angew. Chem. Int. Ed.  2000,  39:  4610 

<A NAME="RT04910SS-13">13</A> Czaplik WM. Mayer M. Jacobi von Wangelin A. Angew. Chem. Int. Ed.  2009,  48:  607 

<A NAME="RT04910SS-14">14</A> Mach K. Antropiusová H. Petrusová L. Turecek F. Hanus V. Sedmera P. Schraml J. J. Organomet. Chem.  1985,  289:  331 

<A NAME="RT04910SS-15">15</A> Mach K. Turecek F. Antropiusová H. Hanus V. J. Organomet. Chem.  1985,  289:  1215