A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds

Heejin Kim, Aiichiro Nagaki, Jun Ichi Yoshida

Research output: Contribution to journalArticle

144 Citations (Scopus)

Abstract

Protecting-group-free synthesis has received significant recent research interest in the context of ideal synthesis and green sustainable chemistry. In general, organolithium species react with ketones very rapidly, and therefore ketone carbonyl groups should be protected before an organolithium reaction, if they are not involved in the desired transformation. If organolithium chemistry could be free from such a limitation, its power would be greatly enhanced. Here we show that a flow microreactor enables such protecting-group-free organolithium reactions by greatly reducing the residence time (0.003 s or less). Aryllithium species bearing ketone carbonyl groups are generated by iodine-lithium exchange reactions of the corresponding aryl iodides with mesityllithium and are reacted with various electrophiles using a flow-microreactor system. The present method has been successfully applied to the formal synthesis of Pauciflorol F.

Original languageEnglish
Article number264
JournalNature communications
Volume2
Issue number1
DOIs
Publication statusPublished - 2011 Apr 13
Externally publishedYes

Fingerprint

Ketones
ketones
Bearings (structural)
synthesis
Iodides
chemistry
Lithium
Iodine
iodides
iodine
lithium
Research

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Physics and Astronomy(all)

Cite this

A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds. / Kim, Heejin; Nagaki, Aiichiro; Yoshida, Jun Ichi.

In: Nature communications, Vol. 2, No. 1, 264, 13.04.2011.

Research output: Contribution to journalArticle

@article{8ddcb90983654427bad90abc48276dd5,
title = "A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds",
abstract = "Protecting-group-free synthesis has received significant recent research interest in the context of ideal synthesis and green sustainable chemistry. In general, organolithium species react with ketones very rapidly, and therefore ketone carbonyl groups should be protected before an organolithium reaction, if they are not involved in the desired transformation. If organolithium chemistry could be free from such a limitation, its power would be greatly enhanced. Here we show that a flow microreactor enables such protecting-group-free organolithium reactions by greatly reducing the residence time (0.003 s or less). Aryllithium species bearing ketone carbonyl groups are generated by iodine-lithium exchange reactions of the corresponding aryl iodides with mesityllithium and are reacted with various electrophiles using a flow-microreactor system. The present method has been successfully applied to the formal synthesis of Pauciflorol F.",
author = "Heejin Kim and Aiichiro Nagaki and Yoshida, {Jun Ichi}",
year = "2011",
month = "4",
day = "13",
doi = "10.1038/ncomms1264",
language = "English",
volume = "2",
journal = "Nature Communications",
issn = "2041-1723",
publisher = "Nature Publishing Group",
number = "1",

}

TY - JOUR

T1 - A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds

AU - Kim, Heejin

AU - Nagaki, Aiichiro

AU - Yoshida, Jun Ichi

PY - 2011/4/13

Y1 - 2011/4/13

N2 - Protecting-group-free synthesis has received significant recent research interest in the context of ideal synthesis and green sustainable chemistry. In general, organolithium species react with ketones very rapidly, and therefore ketone carbonyl groups should be protected before an organolithium reaction, if they are not involved in the desired transformation. If organolithium chemistry could be free from such a limitation, its power would be greatly enhanced. Here we show that a flow microreactor enables such protecting-group-free organolithium reactions by greatly reducing the residence time (0.003 s or less). Aryllithium species bearing ketone carbonyl groups are generated by iodine-lithium exchange reactions of the corresponding aryl iodides with mesityllithium and are reacted with various electrophiles using a flow-microreactor system. The present method has been successfully applied to the formal synthesis of Pauciflorol F.

AB - Protecting-group-free synthesis has received significant recent research interest in the context of ideal synthesis and green sustainable chemistry. In general, organolithium species react with ketones very rapidly, and therefore ketone carbonyl groups should be protected before an organolithium reaction, if they are not involved in the desired transformation. If organolithium chemistry could be free from such a limitation, its power would be greatly enhanced. Here we show that a flow microreactor enables such protecting-group-free organolithium reactions by greatly reducing the residence time (0.003 s or less). Aryllithium species bearing ketone carbonyl groups are generated by iodine-lithium exchange reactions of the corresponding aryl iodides with mesityllithium and are reacted with various electrophiles using a flow-microreactor system. The present method has been successfully applied to the formal synthesis of Pauciflorol F.

UR - http://www.scopus.com/inward/record.url?scp=79953769993&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79953769993&partnerID=8YFLogxK

U2 - 10.1038/ncomms1264

DO - 10.1038/ncomms1264

M3 - Article

VL - 2

JO - Nature Communications

JF - Nature Communications

SN - 2041-1723

IS - 1

M1 - 264

ER -