@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.",
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",
}