Development of Generation Method of Unstable Chemical Species Using Carbon Monoxide

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We investigated the new generation method of unstable chemical species by the use of the characteristics of carbon monoxide and the utilization of these unstable species in organic synthesis. In the course of this study, we found that nitre or nitrenoid species were generated smoothly by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. When 0-nitrostyrenes were treated with carbon monoxide in the presence of a catalytic amount of selenium, deoxyganation of nitro group followed by intramolecular cyclization proceeded efficiently to give the corresponding indols in moderate to good yields. On the reaction of 0-nitrobenzoylamides with carbon monoxide, 4(3H)-quinazolinones were synthesized in moderate to good yields. In addition, we have also developed the rhenium complexes having ligand of carbon monoxide acts as a catalyst on the Friedel-Craft alkylation of arenes with alkyl halides, Aldol type reaction of enol silyl ethers with carbonyl compounds and allylation of carbonyl compounds with allyic stannanes.