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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Sequential Oxidation/Cyclization of Readily Available Imine Linkages to Access Benzoxazole-Linked Covalent Organic
Yanqiu Zhu1,2, Dekang Huang1, Wanqin Wang1,2
1College of Chemistry, Huazhong Agricultural University, Wuhan, 430070, PR China.
Abstract:
Benzoxazole-linked covalent organic frameworks (BO-COFs), despite their exceptional chemical stability, are still in their infancy. This is primarily because the current prevalent methods require the use of special ortho-hydroxyl-substituted aromatic amines as monomers. Herein, we report an innovative strategy to access BO-COFs directly from imine-linked COFs (Im-COFs) without pre-embedded OH groups, using a two-step sequential oxidation/cyclization process. The two-step process included the oxidation of Im-COFs into amide-linked COFs, followed by a copper-catalyzed oxidative cyclization. Five representative BO-COFs were synthesized with retained crystallinity and high oxidization efficiency, offering the potential to convert a significant portion of Im-COFs into BO-COFs. The structural advantages of the newly designed BO-COFs were demonstrated through their application to photocatalytic organic transformations.
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