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A Mild and Versatile Method for the Synthesis of Alkyl Ethers from Methoxymethyl Ethers and Application to the Preparation of Sterically Crowded Ethers
Author(s) -
Minamitsuji Yutaka,
Kawaguchi Atsuhisa,
Kubo Ozora,
Ueyama Yoshifumi,
Maegawa Tomohiro,
Fujioka Hiromichi
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200290
Subject(s) - chemistry , pyridinium , alkyl , steric effects , ether , organic chemistry , salt (chemistry) , williamson ether synthesis , base (topology) , mathematical analysis , mathematics
A mild and divergent route for the synthesis of alkyl ethers from methoxymethyl (MOM) and methoxyethyl (ME) ether derivatives via pyridinium‐type salt intermediates has been developed. The addition of organocuprates to the salts afforded the corresponding alkyl ethers, including highly crowded ones, in high yields even in the presence of acid‐ or base‐sensitive functional groups.