2,3-Dicyano-5,6-dichlorobenzoquinone-Mediated and Selective C–O and C–C Cross-Couplings of Phenols and Porphyrins
2019
Cheng, Qi | Wang, Zheng | Li, Hong-Wei | Shan, Chang-Yu | Zheng, Peng-Fei | Shuai, Li | Li, Yu-Long | Chen, Ying-Chun | Ouyang, Qin
A selective C–O cross-coupling reaction between porphyrins and phenols has been developed through 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)/Sc(OTf)₃ oxidation, efficiently delivering meso-etherified porphyrins in good yields (≤93%). The radical complex process was proposed and calculated as the rationalized mechanism to block the homocoupling process. In addition, the switchable selective C–C cross-coupling reaction was achieved by using bulky electron-rich phenols and naphthols under DDQ oxidation conditions.
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