Construction of C–O bond via cross-dehydrogenative coupling of sp [3] C–H bond with phenols catalyzed by copper porphyrin
Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in moderate to excellent yields with good functio...
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Veröffentlicht in: | Tetrahedron 2020-11, Vol.76 (45), p.131569, Article 131569 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in moderate to excellent yields with good functional group tolerance. The developed method is not only suitable for phenol substrates with ortho-directing groups, but also suitable for those phenol without ortho-directing groups. Significantly, a high turnover number (TON) up to 7300 was achieved in gram-level test.
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•Copper porphyrin-catalyzed construction of C-O bond by coupling of cyclic ether with phenols was described firstly.•The reaction greatly extended the phenol substrate scope for construction of C-O bonds.•The reaction achieved a high turnover number (TON) up to 7300 in gram-level test. |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2020.131569 |