Here, we report a copper acetate/tert-butyl hydroperoxide-mediated reaction of N-substituted indoles with dimethyl carbonate under heating to give tris(indolyl)methanes via alpha-C-H functionalization of the methoxy group of dimethyl carbonate. The central methine carbon in the product comes from the dimethyl carbonate molecule, which is used as a substrate as well as a reaction medium. The reaction uses a cheap and environmentally benign copper metal catalyst which makes the process useful. This is the first report of tris(indolyl)methane synthesis using dimethyl carbonate as a single carbon source.
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Hunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R ChinaHunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R China
Wu, Lijun
Deng, Guobo
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Hunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R ChinaHunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R China
Deng, Guobo
Liang, Yun
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Hunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R ChinaHunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol, Changsha 410081, Hunan, Peoples R China