@article{c9e965d0075b4ffd9b6d87c37ab8e8e5,
title = "Copper-Catalyzed Electrophilic Etherification of Arylboronic Esters with Isoxazolidines",
abstract = "A copper-catalyzed electrophilic etherification of arylboronic esters is reported. Isoxazolidines are utilized as easily available and stable [RO]+ surrogates to give 1,3-amino 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.",
keywords = "aryl ether, chemoselectivity, copper catalyst, electrophilic reaction, isoxazolidine",
author = "Seiya Katahara and Tenga Takahashi and Kengo Nomura and Masanobu Uchiyama and Takaaki Sato and Noritaka Chida",
note = "Funding Information: This research was supported by a Grant‐in‐Aid for Scientific Research (C) from MEXT (No. 18K05127), and a JSPS fellowship to S.K. (No. 19J10048), and Grants‐in‐Aid for Scientific Research (S) (No. 17H06173), and JST CREST (No. JPMJCR19R2) to M.U. Allotment of computational resources (Project G19012) from HOKUSAI BigWaterfall (RIKEN) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = jun,
day = "17",
doi = "10.1002/asia.202000270",
language = "English",
volume = "15",
pages = "1869--1872",
journal = "Chemistry - An Asian Journal",
issn = "1861-4728",
publisher = "John Wiley and Sons Ltd",
number = "12",
}