The mechanism of indeno[1,2,3-de]quinolin-2-one formation

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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The mechanism of indeno[1,2,3-de]quinolin-2-one formation

Cited by 2 publications

References 10 publications

ChemInform Abstract: THE MECHANISM OF INDENO(1,2,3‐DE)QUINOLIN‐2‐ONE FORMATION

ChemInform Abstract: THE MECHANISM OF INDENO(1,2,3‐DE)QUINOLIN‐2‐ONE FORMATION

Direct Oxidative Carbon−Carbon Bond Formation Using the “Cation Pool” Method. 1. Generation of Iminium Cation Pools and Their Reaction with Carbon Nucleophiles

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