Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 36, Pages 11167-11177Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000876
Keywords
aryllithium; flash chemistry; microreactors; organometallic compounds; protecting groups
Categories
Funding
- JSPS [20245008, 20750077]
- NEDO
- Grants-in-Aid for Scientific Research [22750092, 21106002] Funding Source: KAKEN
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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 sBuLi 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 sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.
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