A copper-catalyzed electrophilic etherification of arylboronic esters is reported. Isoxazolidines are utilized as easily available and stable [RO] + surrogates to give 1,3amino aryl ethers. The O-selective arylation of isoxazolidines takes place without causing competitive N-arylation. In contrast to previously reported anionic conditions, our copper-catalyzed conditions are mild enough to achieve high functional group tolerance. Preliminary mechanistic studies and DFT calculations support that the reaction proceeds via a transmetalation/oxidative addition pathway, followed by a Lewis acid-promoted reductive elimination to induce the crucial O-selectivity. Aromatic ethers are important functional groups in a wide range of molecules with numerous applications such as biologically active compounds and pharmaceuticals. [1] Transition metal-catalyzed formation of carbonÀ oxygen bonds have been extensively studied as one of the promising methods to generate aromatic ethers. To date, most coupling reactions that construct carbonÀ oxygen bonds utilize nucleophilic oxygen atoms and electrophilic carbon centers as seen in the Ullman-Goldberg coupling [2] and the Buchwald-Hartwig coupling. [3] Oxidative Chan-Evans-Lam coupling [4] using boronic acids is another promising approach. However, few examples of electrophilic etherification have been reported in spite of its potential utility.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
customersupport@researchsolutions.com
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.