Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane

In situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borina...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 14; pp. 3532 - 3535
Main Authors Marciasini, Ludovic, Cacciuttolo, Bastien, Vaultier, Michel, Pucheault, Mathieu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.07.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOBORON COMPOUNDS
DIARYLBORINIC ACIDS
MILD CONDITIONS
ANALOGS
2-AMINOETHYL DIPHENYLBORINATE 2-APB
IDENTIFICATION
PALLADIUM NANOCRYSTALS
ARYL CHLORIDES
BORYLATION
CATALYSTS
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Summary:In situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borinates adducts, with ethanolamine or 8-hydroxyquinoline, after workup.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01620