Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles

A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1-bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at −70 °C. In the subsequent reactor o-bromoph...

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Published inJournal of the American Chemical Society Vol. 136; no. 35; pp. 12245 - 12248
Main Authors Nagaki, Aiichiro, Ichinari, Daisuke, Yoshida, Jun-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.09.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIDATION
REACTORS
INSERTION
REDUCTION
SPACE INTEGRATION
GENERATION
ARYNES
EFFICIENT
FLOW-MICROREACTOR APPROACH
EXCHANGE-REACTIONS
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Abstract A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1-bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at −70 °C. In the subsequent reactor o-bromophenyllithium is decomposed to generate benzyne without affecting the functionalized aryllithium at −30 °C, and carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature–residence time mapping is responsible for the success of the present transformation. The present method has been successfully applied to the synthesis of boscalid.
AbstractList A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1-bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at -70 degrees C. In the subsequent reactor o-bromophenyllithium is decomposed to generate benzyne without affecting the functionalized aryllithium at -30 degrees C, and carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature-residence time mapping is responsible for the success of the present transformation. The present method has been successfully applied to the synthesis of boscalid.
A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1-bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at -70 °C. In the subsequent reactor o-bromophenyllithium is decomposed to generate benzyne without affecting the functionalized aryllithium at -30 °C, and carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature-residence time mapping is responsible for the success of the present transformation. The present method has been successfully applied to the synthesis of boscalid.
A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from 1-bromo-2-iodobenzene and a functionalized aryllithium generated from the corresponding aryl halide were mixed at −70 °C. In the subsequent reactor o-bromophenyllithium is decomposed to generate benzyne without affecting the functionalized aryllithium at −30 °C, and carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature–residence time mapping is responsible for the success of the present transformation. The present method has been successfully applied to the synthesis of boscalid.
Author Ichinari, Daisuke
Nagaki, Aiichiro
Yoshida, Jun-ichi
AuthorAffiliation Kyoto University
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering
AuthorAffiliation_xml – name: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering
– name: Kyoto University
Author_xml – sequence: 1
  givenname: Aiichiro
  surname: Nagaki
  fullname: Nagaki, Aiichiro
– sequence: 2
  givenname: Daisuke
  surname: Ichinari
  fullname: Ichinari, Daisuke
– sequence: 3
  givenname: Jun-ichi
  surname: Yoshida
  fullname: Yoshida, Jun-ichi
  email: yoshida@sbchem.kyoto-u.ac.jp
BackLink https://www.ncbi.nlm.nih.gov/pubmed/25153763$$D View this record in MEDLINE/PubMed
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Issue 35
Keywords OXIDATION
REACTORS
INSERTION
REDUCTION
SPACE INTEGRATION
GENERATION
ARYNES
EFFICIENT
FLOW-MICROREACTOR APPROACH
EXCHANGE-REACTIONS
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Snippet A flow microreactor method for three-component coupling of benzyne was developed based on flash chemistry. o-Bromophenyllithium generated from...
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SubjectTerms Chemistry
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Title Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles
URI http://dx.doi.org/10.1021/ja5071762
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