Novel Highly Stereoselective Approach toward (Z)-1,2-Bis(silyl)ethenes

Abstract

A new flexible and stereoselective protocol for the synthesis of the compounds of the general formula, (Z)-Ph₂RSiCH=CHSiRPh₂ (where R is an alkyl, alkenyl or alkoxy substituent) has been developed. The title compounds have been efficiently obtained by ruthenium hydride complex [RuHCl(CO)(PCy₃)₂]-catalyzed (Z)-selective silylative coupling cyclization of 1,2-bis(diphenylvinylsiloxy)ethane or N,N′-dimethyl-N,N′-di(diphenylvinylsilyl)ethane-1,2-diamine to generate respective disilacyclic platforms, followed by their reaction with Grignard reagents or alcohols. (Z)-Bis(silyl)ethenes could not be synthesized by a metathesis procedure.

vinylsilanes - silylative coupling - ruthenium complex - Grignard reagent - cyclization

References

<A NAME="RT07806SS-1A">1a</A> Colvin EW. Silicon Reagents in Organic Synthesis   Academic Press; London: 1988. 

<A NAME="RT07806SS-1B">1b</A> The Chemistry of Organosilicon Compounds   Patai S. Rappoport Z. Wiley; Chichester: 1988.  Chap. 3.

<A NAME="RT07806SS-1C">1c</A> Fleming I. Barbero A. Walter D. Chem. Rev.  1997,  97:  2063 

<A NAME="RT07806SS-1D">1d</A> Oshima K. In Science of Synthesis   Vol. 4:  Fleming I. Thieme; Stuttgart: 2002.  Chap. 4.4.34.

<A NAME="RT07806SS-2A">2a</A> Hagiwara E. Gouda K. Hatanaka Y. Hiyama T. Tetrahedron Lett.  1997,  38:  439 

<A NAME="RT07806SS-2B">2b</A> Karabelas K. Hallberg A. J. Org. Chem.  1989,  54:  1773 

For reviews, see:

<A NAME="RT07806SS-3A">3a</A> Marciniec B. Pietraszuk C. Kownacki I. Zaidlewicz M. Vinyl- and Aryl Silicon, Germanium, and Boron Compounds, In Comprehensive Organic Functional Group Transformations II   Vol. 2:  Katritzky AR. Taylor JK. Elsevier; Oxford: 2005.  p.941-1023  ; and references cited therein

<A NAME="RT07806SS-3B">3b</A> Horn KA. Chem. Rev.  1995,  95:  1317 

<A NAME="RT07806SS-3C">3c</A> Sharma HK. Pannel KH. Chem. Rev.  1995,  95:  1351 

<A NAME="RT07806SS-3D">3d</A> Beletskaya I. Moberg Ch. Chem. Rev.  1999,  99:  3435 

<A NAME="RT07806SS-3E">3e</A> Suginome M. Ito Y. Chem. Rev.  2000,  100:  7654 

For recent examples, see:

<A NAME="RT07806SS-4A">4a</A> Wu W. Li Ch. Chem. Commun.  2003,  1668 

<A NAME="RT07806SS-4B">4b</A> Asao N. Sudo T. Yamamoto Y. J. Org. Chem.  1996,  61:  7654 

<A NAME="RT07806SS-5">5</A> Marciniec B. Pietraszuk C. In Handbook of Metathesis   Vol. 2:  Grubbs RH. Wiley-VCH; Weinheim: 2003.  Chap. 13.

<A NAME="RT07806SS-6A">6a</A> Obora Y. Moriya H. Tokunaga M. Tsuji Y. Chem. Commun.  2003,  2820 

<A NAME="RT07806SS-6B">6b</A> Eisch JJ. Gitua JN. Organometallics  2003,  22:  24 

<A NAME="RT07806SS-6C">6c</A> Barbero A. Cuadrado P. Fleming I. Gonzalez AM. Pulido FJ. Sanchez A. J. Chem. Soc., Perkin Trans. 1  1995,  1525 

For reviews, see:

<A NAME="RT07806SS-7A">7a</A> Marciniec B. Coord. Chem. Rev.  2005,  249:  2374 

<A NAME="RT07806SS-7B">7b</A> Marciniec B. Pietraszuk C. Curr. Org. Chem.  2003,  7:  691 

<A NAME="RT07806SS-8A">8a</A> Majchrzak M. Marciniec B. Itami Y. Adv. Synth. Catal.  2005,  347:  1285 

<A NAME="RT07806SS-8B">8b</A> Marciniec B. Lewandowski M. Tetrahedron Lett.  1997,  38:  3777 

<A NAME="RT07806SS-8C">8c</A> Marciniec B. Pietraszuk C. J. Organomet. Chem.  1991,  412:  C1 

<A NAME="RT07806SS-9A">9a</A> Marciniec B. Maecka E. Macromol. Rapid Commun.  1999,  20:  475 

<A NAME="RT07806SS-9B">9b</A> Majchrzak M. Itami Y. Marciniec B. Pawluc P. Tetrahedron Lett.  2000,  41:  10303 

<A NAME="RT07806SS-9C">9c</A> Marciniec B. Maecka E. Œcibiorek M. Macromolecules  2003,  36:  5545 

<A NAME="RT07806SS-9D">9d</A> Marciniec B. Maecka E. J. Phys. Org. Chem.  2003,  16:  818 

<A NAME="RT07806SS-10A">10a</A> Wakatsuki Y. Yamazaki H. Nakano N. Yamamoto Y. J. Chem. Soc., Chem. Commun.  1991,  703 

<A NAME="RT07806SS-10B">10b</A> Marciniec B. Pietraszuk C. J. Chem. Soc., Chem. Commun.  1995,  2003 

<A NAME="RT07806SS-10C">10c</A> Marciniec B. Pietraszuk C. Organometallics  1997,  16:  4320 

<A NAME="RT07806SS-11A">11a</A> Pawluc P. Marciniec B. Hreczycho G. Gaczewska B. Itami Y. J. Org. Chem.  2005,  70:  370 

<A NAME="RT07806SS-11B">11b</A> Pawluc P. Hreczycho G. Marciniec B. Synlett  2005,  1105 

<A NAME="RT07806SS-12">12</A> Majchrzak M. Marciniec B. Kubicki M. Pawelczyk A. Organometallics  2005,  24:  3731 

<A NAME="RT07806SS-13A">13a</A> Jankowska M. Shuvalova O. Bespalova N. Majchrzak M. Marciniec B. J. Organomet. Chem.  2005,  690:  4492 

<A NAME="RT07806SS-13B">13b</A> Jankowska M. Marciniec B. Pietraszuk C. Cytarska J. Zaidlewicz M. Tetrahedron Lett.  2005,  45:  6615 

<A NAME="RT07806SS-14">14</A>

Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-292109. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: [phone];
e-mail: [e-mail]).

<A NAME="RT07806SS-15">15</A> Yi CS. Lee DW. Chen Y. Organometallics  1999,  18:  2043