Radical α-addition involved electrooxidative [3 + 2] annulation of phenols and electron-deficient alkenes |
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| Authors: | Qiang Zhao Ji-Kang Jin Jie Wang Feng-Lian Zhang Yi-Feng Wang |
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| Institution: | Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis of CAS, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei Anhui 230026 China, |
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| Abstract: | An electrooxidative 3 + 2] annulation of phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives was achieved. The ring construction starts by a unique α-addition of carbon radicals derived from anodic oxidation of phenols to electron-deficient alkenes. The subsequent anodic oxidation of the resulting alkyl radical intermediates followed by trapping with the phenolic hydroxy group assembles the 2,3-dihydrobenzofuran core. Such a pathway enables the installation of various electrophilic functionalities including alkoxycarbonyl, alkylaminocarbonyl, trifluoromethyl, and cyano groups at the C-3 of the 2,3-dihydrobenzofuran framework, which is unattainable by other intermolecular reactions. The application of this method for a rapid synthesis of a bioactive natural product is demonstrated.An electrooxidative 3 + 2] annulation between phenols and electron-deficient alkenes for the synthesis of C3-functionalized 2-aryl-2,3-dihydrobenzofuran derivatives is described. |
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