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.

Key words

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

References

• 1a Colvin EW. Silicon Reagents in Organic Synthesis   Academic Press; London: 1988. 
• 1b The Chemistry of Organosilicon Compounds   Patai S. Rappoport Z. Wiley; Chichester: 1988.  Chap. 3.
• 1c Fleming I. Barbero A. Walter D. Chem. Rev.  1997,  97:  2063 
• 1d Oshima K. In Science of Synthesis   Vol. 4:  Fleming I. Thieme; Stuttgart: 2002.  Chap. 4.4.34.
• 2a Hagiwara E. Gouda K. Hatanaka Y. Hiyama T. Tetrahedron Lett.  1997,  38:  439 
• 2b Karabelas K. Hallberg A. J. Org. Chem.  1989,  54:  1773 
• For reviews, see:
• 3a 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
• 3b Horn KA. Chem. Rev.  1995,  95:  1317 
• 3c Sharma HK. Pannel KH. Chem. Rev.  1995,  95:  1351 
• 3d Beletskaya I. Moberg Ch. Chem. Rev.  1999,  99:  3435 
• 3e Suginome M. Ito Y. Chem. Rev.  2000,  100:  7654 
• For recent examples, see:
• 4a Wu W. Li Ch. Chem. Commun.  2003,  1668 
• 4b Asao N. Sudo T. Yamamoto Y. J. Org. Chem.  1996,  61:  7654 
• 5 Marciniec B. Pietraszuk C. In Handbook of Metathesis   Vol. 2:  Grubbs RH. Wiley-VCH; Weinheim: 2003.  Chap. 13.
• 6a Obora Y. Moriya H. Tokunaga M. Tsuji Y. Chem. Commun.  2003,  2820 
• 6b Eisch JJ. Gitua JN. Organometallics  2003,  22:  24 
• 6c Barbero A. Cuadrado P. Fleming I. Gonzalez AM. Pulido FJ. Sanchez A. J. Chem. Soc., Perkin Trans. 1  1995,  1525 
• For reviews, see:
• 7a Marciniec B. Coord. Chem. Rev.  2005,  249:  2374 
• 7b Marciniec B. Pietraszuk C. Curr. Org. Chem.  2003,  7:  691 
• 8a Majchrzak M. Marciniec B. Itami Y. Adv. Synth. Catal.  2005,  347:  1285 
• 8b Marciniec B. Lewandowski M. Tetrahedron Lett.  1997,  38:  3777 
• 8c Marciniec B. Pietraszuk C. J. Organomet. Chem.  1991,  412:  C1 
• 9a Marciniec B. Maecka E. Macromol. Rapid Commun.  1999,  20:  475 
• 9b Majchrzak M. Itami Y. Marciniec B. Pawluc P. Tetrahedron Lett.  2000,  41:  10303 
• 9c Marciniec B. Maecka E. Œcibiorek M. Macromolecules  2003,  36:  5545 
• 9d Marciniec B. Maecka E. J. Phys. Org. Chem.  2003,  16:  818 
• 10a Wakatsuki Y. Yamazaki H. Nakano N. Yamamoto Y. J. Chem. Soc., Chem. Commun.  1991,  703 
• 10b Marciniec B. Pietraszuk C. J. Chem. Soc., Chem. Commun.  1995,  2003 
• 10c Marciniec B. Pietraszuk C. Organometallics  1997,  16:  4320 
• 11a Pawluc P. Marciniec B. Hreczycho G. Gaczewska B. Itami Y. J. Org. Chem.  2005,  70:  370 
• 11b Pawluc P. Hreczycho G. Marciniec B. Synlett  2005,  1105 
• 12 Majchrzak M. Marciniec B. Kubicki M. Pawelczyk A. Organometallics  2005,  24:  3731 
• 13a Jankowska M. Shuvalova O. Bespalova N. Majchrzak M. Marciniec B. J. Organomet. Chem.  2005,  690:  4492 
• 13b Jankowska M. Marciniec B. Pietraszuk C. Cytarska J. Zaidlewicz M. Tetrahedron Lett.  2005,  45:  6615 
• 15 Yi CS. Lee DW. Chen Y. Organometallics  1999,  18:  2043 

14

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]).