Palladium-catalyzed carbostannylation by means of reagents containing carbon–tin–halogen inter-element linkages

Reagents containing carbon–tin–halogen inter-element linkages were effective for palladium-catalyzed carbostannylation. In situ generated allyltin trichlorides add to carbon–carbon double bonds of bicyclo[2.2.1]hept-2-ene (norbornene) and bicyclo[2.2.1]hepta-2,5-diene (norbornadiene), stereoselectiv...

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Bibliographic Details
Published in:Journal of organometallic chemistry 2000-10, Vol.611 (1), p.433-444
Main Authors: Fugami, Keigo, Kawata, Kentaro, Enokido, Tatsuki, Mishiba, Yukie, Hagiwara, Sachiko, Hirunuma, Yasuyuki, Koyama, Daisuke, Kameyama, Masayuki, Kosugi, Masanori
Format: Article
Language:English
Subjects:
Alkenes
Allylation
Arylation
Palladium and compounds
Tin and compounds
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Summary:Reagents containing carbon–tin–halogen inter-element linkages were effective for palladium-catalyzed carbostannylation. In situ generated allyltin trichlorides add to carbon–carbon double bonds of bicyclo[2.2.1]hept-2-ene (norbornene) and bicyclo[2.2.1]hepta-2,5-diene (norbornadiene), stereoselectively, under the catalysis of palladium(0) species in good yields. The regioselectivity of unsymmetrically substituted allylic reagents dramatically alters with the choice of the tin(II) salt. Aryltin trichlorides undergo palladium-catalyzed arylstannylation of norbornene, giving a mixture of products composed of that taking one norbornene and that taking two norbornenes. The product ratio is dependent on the choice of the solvent and electronic nature of the aromatic substituent.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(00)00483-6