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Copper‐Catalyzed Electrophilic Etherification of Arylboronic Esters with Isoxazolidines
Author(s) -
Katahara Seiya,
Takahashi Tenga,
Nomura Kengo,
Uchiyama Masanobu,
Sato Takaaki,
Chida Noritaka
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000270
Subject(s) - transmetalation , chemistry , electrophile , catalysis , lewis acids and bases , selectivity , reductive elimination , aryl , combinatorial chemistry , copper , functional group , organic chemistry , alkyl , polymer
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.