A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

Aiichiro Nagaki; Heejin Kim; Yuya Moriwaki; Chika Matsuo; Jun Ichi Yoshida

doi:10.1002/chem.201000876

A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

Aiichiro Nagaki, Heejin Kim, Yuya Moriwaki, Chika Matsuo, Jun Ichi Yoshida

Research output: Contribution to journal › Article › peer-review

91 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	11167-11177
Number of pages	11
Journal	Chemistry - A European Journal
Volume	16
Issue number	36
DOIs	https://doi.org/10.1002/chem.201000876
Publication status	Published - 2010 Sept 24
Externally published	Yes

Keywords

Aryllithium
Flash chemistry
Microreactors
Organometallic compounds
Protecting groups

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201000876

Cite this

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title = "A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups",

abstract = "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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author = "Aiichiro Nagaki and Heejin Kim and Yuya Moriwaki and Chika Matsuo and Yoshida, {Jun Ichi}",

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T1 - A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

AU - Nagaki, Aiichiro

AU - Kim, Heejin

AU - Moriwaki, Yuya

AU - Matsuo, Chika

AU - Yoshida, Jun Ichi

PY - 2010/9/24

Y1 - 2010/9/24

N2 - 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.

AB - 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.

KW - Aryllithium

KW - Flash chemistry

KW - Microreactors

KW - Organometallic compounds

KW - Protecting groups

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DO - 10.1002/chem.201000876

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

Abstract

Keywords

ASJC Scopus subject areas

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