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Synthesis 2021; 53(15): 2665-2675
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

Raed M. Al-Zoubi  ∗
a   Department of Chemistry, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan
b   Surgical Research Section, Department of Surgery, Hamad Medical Corporation, Doha, Qatar
,
Reem M. Altamimi
a   Department of Chemistry, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan
,
Walid K. Al-Jammal
a   Department of Chemistry, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan
,
Khaled Q. Shawakfeh
a   Department of Chemistry, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan
,
Mazhar S. Al-Zoubi
c   Department of Basic Medical Sciences, Faculty of Medicine, Yarmouk University, Irbid, Jordan
,
Michael J. Ferguson
d   Department of Chemistry, Gunning-Lemieux Chemistry Centre, University of Alberta, Edmonton, Alberta T6G2G2, Canada
,
Ahmad Zarour
b   Surgical Research Section, Department of Surgery, Hamad Medical Corporation, Doha, Qatar
,
Aksam Yassin
b   Surgical Research Section, Department of Surgery, Hamad Medical Corporation, Doha, Qatar
,
Abdulla Al-Ansari
b   Surgical Research Section, Department of Surgery, Hamad Medical Corporation, Doha, Qatar
› InstitutsangabenThis work was generously funded by Jordan University of Science and Technology (JUST) - Deanship of Research - Jordan (Grant No. 98/2019 for R.M.A.).
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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 - catalyst

Supporting Information



Publikationsverlauf

Eingereicht: 15. Januar 2021

Angenommen nach Revision: 22. März 2021

Accepted Manuscript online:
22. März 2021

Artikel online veröffentlicht:
12. April 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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