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.
Original language | English |
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Pages (from-to) | 1869-1872 |
Number of pages | 4 |
Journal | Chemistry - An Asian Journal |
Volume | 15 |
Issue number | 12 |
DOIs | |
Publication status | Published - 2020 Jun 17 |
Keywords
- aryl ether
- chemoselectivity
- copper catalyst
- electrophilic reaction
- isoxazolidine
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry