TY - JOUR
T1 - Novel carbon-carbon bond formation through Mizoroki-Heck type reaction of silanols and organotin compounds
AU - Hirabayashi, Kazunori
AU - Ando, Jun Ichi
AU - Kawashima, Jun
AU - Nishihara, Yasushi
AU - Mori, Atsunori
AU - Hiyama, Tamejiro
PY - 2000/6
Y1 - 2000/6
N2 - The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)2 or by a combined use of 0.1 molar amount of Pd(OAc)2 and Cu(OAc)2/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the sitanol, although the tin reagent sometimes induced undesirable homocoupling, while the reaction with silanol did not give such by-product.
AB - The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)2 or by a combined use of 0.1 molar amount of Pd(OAc)2 and Cu(OAc)2/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the sitanol, although the tin reagent sometimes induced undesirable homocoupling, while the reaction with silanol did not give such by-product.
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U2 - 10.1246/bcsj.73.1409
DO - 10.1246/bcsj.73.1409
M3 - Article
AN - SCOPUS:0034045753
VL - 73
SP - 1409
EP - 1417
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 6
ER -