Cationic Palladium Complex-catalyzed Cyclization-Hydrosilylation of 1-Alkene-6,11-diyne Derivatives : Facile Cyclization at the Enyne Part than at the Diyne Counterpart
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A palladium complex, [(η<SUP>3</SUP>-C<SUB>3</SUB>H<SUB>5</SUB>)Pd(cod)]<SUP>+</SUP>[PF<SUB>6</SUB>]<SUP>−</SUP> (<B>C</B>), catalyzes hydrosilylation of 1-dodecene-6,11-diyne (<B>5</B>) or 1-tridecene-6,11-diyne (<B>7</B>), and of their 9-oxo congeners (<B>9</B> or <B>11</B>), with HSiCl<SUB>3</SUB> to form regioisomeric cyclization products (<B>6</B>, <B>8</B>, <B>10</B>, and <B>12</B>, respectively), which arise between the diyne part (path a) to form <B>A</B> series or between the enyne counterpart (path b) to form <B>B</B> series. The formation of product <B>B</B> is markedly favored with 1-tridecene-6,11-diyne derivatives as compared with 1-dodecene-6,11-diyne ones that possess a terminal alkyne.
- Chemistry Letters
Chemistry Letters 35(8), 846-847, 2006-08-05
The Chemical Society of Japan