TY - JOUR
T1 - Chain-walking strategy for organic synthesis
T2 - Catalytic cycloisomerization of 1,n-dienes
AU - Kochi, Takuya
AU - Hamasaki, Taro
AU - Aoyama, Yuka
AU - Kawasaki, Junichi
AU - Kakiuchi, Fumitoshi
PY - 2012/10/10
Y1 - 2012/10/10
N2 - The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/ hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.
AB - The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/ hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.
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U2 - 10.1021/ja308377u
DO - 10.1021/ja308377u
M3 - Article
C2 - 22998107
AN - SCOPUS:84867345621
SN - 0002-7863
VL - 134
SP - 16544
EP - 16547
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 40
ER -