Titanocene-catalyzed double silylation of dienes and aryl alkenes with chlorosilanes

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9697-9698

  Terao, Jun ^a   Kambe, Nobuaki ^a   Sonoda, Noboru ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

Alkenes; Chlorosilanes; Dienes; Double Silylation; Grignard reagents; Titanium and compounds

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; TITANOCENE;

ARTICLE; CATALYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0032564644     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02227-8     Document Type: Article

References (9)

1. [1] For a review, see: Horn KA. Chem. Rev. 1995;95:1317-1350. See also: Sakaki S, Ogawa M, Musashi Y. J. Organomet. Chem. 1997;535:25-28 and references therein.
2. [1] For a review, see: Horn KA. Chem. Rev. 1995;95:1317-1350. See also: Sakaki S, Ogawa M, Musashi Y. J. Organomet. Chem. 1997;535:25-28 and references therein.
3. 2Cl with acetylenes catalyzed by Pd complexes, see: Tanaka Y, Yamashita H, Tanaka M. Organometallics 1995;14:530-541.
4. 2Cl with acetylenes catalyzed by Pd complexes, see: Tanaka Y, Yamashita H, Tanaka M. Organometallics 1995;14:530-541.
5. [3] We have also found that double alkylation of aryl alkenes with alkyl halides proceeds under similar conditions to give 1,2-dialkylated products: J. Am. Chem. Soc., in press.
6. 3 (Marciniec B, Pietraszuk C, Foltynowicz Z. J. Organomet. Chem. 1994;474:83-87), since sufficient spectral data are not available for 1b. The products 1a-c (as a mixture of stereoisomers) and 2a, b were obtained in pure form by HPLC in 86%, 62%, 76%, 66%, 54% yields, respectively.
7. nBuMgCl, and butadiene, which was condensed at 0 °C under slightly reduced pressure, in a glass vessel equipped with a dry ice condenser.
8. 3SiCl afforded only poor yields of the desired products (<10%) when styrenes were used as the substrates.
9. 2Cl: C, 70.46; H, 7.15. Found: C, 70.41; H, 7.22.