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A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups
Author(s) -
Nagaki Aiichiro,
Kim Heejin,
Moriwaki Yuya,
Matsuo Chika,
Yoshida Junichi
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000876
Subject(s) - microreactor , electrophile , alkyl , chemistry , combinatorial chemistry , flow chemistry , organic chemistry , catalysis
A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para ‐, meta ‐, and ortho ‐positions. Alkyl p ‐ and m ‐lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with s BuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o ‐lithiobenzoates were successfully generated by the Br/Li exchange reaction with s BuLi. Subsequent reactions with electrophiles gave the desired products in good yields.