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Heterocycle compounds synthesized by amide ligand-promoted copper salt catalyzed construction of C-O(S) bonds.

ABSTRACT: We introduce a mild method for the ligand-promoted copper-catalyzed coupling of 2-halophenol to construct DBDO using cost-effective copper salts, ligands, and alkaline reagents. This method cleverly makes 2-bromophenol complete the Ullman reaction twice, achieves efficient C-O(S) bond coupling and intermolecular cyclization, and yields high amounts of oxygen(sulfur)-containing six-membered ring products. Less reactive 2-chlorophenol was also applied in this catalytic system. The application range of the copper-amide catalytic system was further expanded. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.

SUBMITTER: Yin R

PROVIDER: S-EPMC10964132 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Heterocycle compounds synthesized by amide ligand-promoted copper salt catalyzed construction of C-O(S) bonds.

Yin Ruiting R Liu Hailong H Yang Xue X Zhou Xiaoyu X Chen Xia X Li Shenmin S

RSC advances 20240326 14

We introduce a mild method for the ligand-promoted copper-catalyzed coupling of 2-halophenol to construct DBDO using cost-effective copper salts, ligands, and alkaline reagents. This method cleverly makes 2-bromophenol complete the Ullman reaction twice, achieves efficient C-O(S) bond coupling and intermolecular cyclization, and yields high amounts of oxygen(sulfur)-containing six-membered ring products. Less reactive 2-chlorophenol was also applied in this catalytic system. The application rang ...[more]

PMID: 38533100

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