TY - JOUR
T1 - Generation of carbon free radicals by reduction of the cation pool
AU - Suga, Seiji
AU - Suzuki, Shinkiti
AU - Maruyama, Tomokazu
AU - Yoshida, Jun Ichi
PY - 2004/8/1
Y1 - 2004/8/1
N2 - The electrochemical reduction of N-acyliminium ions, which were generated by the "cation pool" method, led to the formation of carbon free radicals. Carbon radicals thus generated underwent homo-coupling reactions and the reactions with activated olefins, such as methyl acrylate. In the latter case, a mechanism involving the addition of a carbon radical to the carbon-carbon double bond, followed by one-electron reduction to give carbanions, has been proposed. The present study opens a new possibility for radical-mediated carbon-carbon bond formation based on the reduction of carbocations.
AB - The electrochemical reduction of N-acyliminium ions, which were generated by the "cation pool" method, led to the formation of carbon free radicals. Carbon radicals thus generated underwent homo-coupling reactions and the reactions with activated olefins, such as methyl acrylate. In the latter case, a mechanism involving the addition of a carbon radical to the carbon-carbon double bond, followed by one-electron reduction to give carbanions, has been proposed. The present study opens a new possibility for radical-mediated carbon-carbon bond formation based on the reduction of carbocations.
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U2 - 10.1246/bcsj.77.1545
DO - 10.1246/bcsj.77.1545
M3 - Article
AN - SCOPUS:4444362718
SN - 0009-2673
VL - 77
SP - 1545
EP - 1554
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 8
ER -