No.140
Vinylation of Aryl and Alkenyl Halide
| T2523 | 2,4,6,8-Tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane (1) |
5g 25g |
Vinylpolysiloxane 1 rapidly undergoes cross-coupling reactions with aryl bromides in the presence of tetrabutylammonium fluoride and Pd catalysts under mild conditions to give coupling vinylation products in high yield.1)
Stem-type dendrimers are synthesized by the reaction of 1 as the core with an excess of trichlorosilane in the presence of a Pt/C catalyst.2)
References
1) Vinylation of aryl and alkenyl halides using the vinylpolysiloxane
a) S. E. Denmark, C. R. Butler, Org. Lett. 2006, 8, 63[DOI]. b) S. E. Denmark, S.-M. Yang, Tetrahedron 2004, 60, 9695[DOI]. c) S. E. Denmark, Z. Wang, J. Organomet. Chem. 2001, 624, 372[DOI].
2) Synthesis of carbosilane dendrimers
C. Kim, H. Kim, Synthesis 2005, 381[DOI].
a) S. E. Denmark, C. R. Butler, Org. Lett. 2006, 8, 63[DOI]. b) S. E. Denmark, S.-M. Yang, Tetrahedron 2004, 60, 9695[DOI]. c) S. E. Denmark, Z. Wang, J. Organomet. Chem. 2001, 624, 372[DOI].
2) Synthesis of carbosilane dendrimers
C. Kim, H. Kim, Synthesis 2005, 381[DOI].
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