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. 2024 Mar 26;14(14):10034-10038.
doi: 10.1039/d4ra00701h. eCollection 2024 Mar 20.

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

Ruiting Yin  1 , Hailong Liu  2 , Xue Yang  1 , Xiaoyu Zhou  2 , Xia Chen  2 , Shenmin Li  1
Affiliations

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

Ruiting Yin et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Selected drugs containing the core skeleton of dibenzo-p-dioxins.
Scheme 2
Scheme 2. Previous synthetic methods for dibenzo-p-dioxins and the present catalytic system.
Scheme 3
Scheme 3. Scaled-up reaction for the formation of DBDO.
Scheme 4
Scheme 4. Possible mechanism for the formation of DBDO by CuCl/L15-catalyzed coupling of 2-bromophenol.
See this image and copyright information in PMC

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