TY - JOUR
T1 - Direct oxidative carbon-carbon bond formation using the 'cation pool' Method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles
AU - Yoshida, Jun Ichi
AU - Suga, Seiji
AU - Suzuki, Shinkiti
AU - Kinomura, Naoya
AU - Yamamoto, Atsushi
AU - Fujiwara, Kazuyuki
PY - 1999/10/20
Y1 - 1999/10/20
N2 - We have developed a method that involves the generation of a 'cation pool' using low-temperature electrolysis, and then its reaction with nucleophiles under non-oxidative conditions. This one-pot method solves problems associated with conventional oxidative generation of cations and their in situ reaction with nucleophiles, and provides an efficient method for direct oxidative carbon-carbon bond formation. As an example of this method, generation of cation pools from carbamates by low-temperature electrolysis (-72 °C) and their reactions with carbon nucleophiles such as allylsilanes, enol silyl ethers, and enol acetates were examined and the desired products were obtained in good yields. Aromatic compounds and 1,3- dicarbonyl compounds can also be utilized as carbon nucleophiles. The present method was also applied to combinatorial parallel synthesis using a robotic synthesizer.
AB - We have developed a method that involves the generation of a 'cation pool' using low-temperature electrolysis, and then its reaction with nucleophiles under non-oxidative conditions. This one-pot method solves problems associated with conventional oxidative generation of cations and their in situ reaction with nucleophiles, and provides an efficient method for direct oxidative carbon-carbon bond formation. As an example of this method, generation of cation pools from carbamates by low-temperature electrolysis (-72 °C) and their reactions with carbon nucleophiles such as allylsilanes, enol silyl ethers, and enol acetates were examined and the desired products were obtained in good yields. Aromatic compounds and 1,3- dicarbonyl compounds can also be utilized as carbon nucleophiles. The present method was also applied to combinatorial parallel synthesis using a robotic synthesizer.
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U2 - 10.1021/ja9920112
DO - 10.1021/ja9920112
M3 - Article
AN - SCOPUS:0032705881
VL - 121
SP - 9546
EP - 9549
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 41
ER -