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Synthesis 2021; 53(15): 2665-2675
DOI: 10.1055/a-1458-2980
DOI: 10.1055/a-1458-2980
paper
CuI-Catalyzed Ullmann-Type Coupling of Phenols and Thiophenols with 5-Substituted 1,2,3-Triiodobenzenes: Facile Synthesis of Mammary Carcinoma Inhibitor BTO-956 in One Step
This work was generously funded by Jordan University of Science and Technology (JUST) - Deanship of Research - Jordan (Grant No. 98/2019 for R.M.A.).
Abstract
A facile and unprecedented synthesis of 2,3-diiodinated or 2,6-diiodinated diaryl ether/thioether derivatives through regioselective Ullmann-type cross couplings of 5-substituted 1,2,3-triiodobenzenes and phenols/thiophenols is described. Remarkably, the coupling reactions are simply controlled by the type of nucleophiles and the nature of C5 substituent at 1,2,3-triiodoarenes providing the internal or terminal coupling products in high regioselectivity and good isolated yields. Noticeable steric and electronic effects were clearly observed on both 1,2,3-triiodoarenes and nucleophiles. The highest yields were isolated from a combination between either electron-poor 1,2,3-triiodoarenes and phenols or electron-rich 1,2,3-triiodoarenes and thiophenols. The optimized conditions were found to be suitable for several functional groups. Using this methodology, mammary carcinoma inhibitor BTO-956 is prepared in only one step with excellent regioselectivity and good isolated yield. This report discloses the first method to prepare 2,3-diiodinated and 2,6-diiodinated diaryl ethers/thioethers in one step that is efficient, regioselective, and general in scope. The products are truly remarkable precursors for other transformations.
Key words
ortho-diiododiaryl ethers/thioethers - BTO-956 - Ullmann-type coupling - substituent effect - catalystSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1458-2980.
- Supporting Information
- CIF File
Publication History
Received: 15 January 2021
Accepted after revision: 22 March 2021
Accepted Manuscript online:
22 March 2021
Article published online:
12 April 2021
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