One-Pot Synthesis of Arylboronic Acids and Aryl Trifluoroborates by Ir-Catalyzed Borylation of Arenes

The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, th...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 5; pp. 757 - 760
Main Authors Murphy, Jaclyn M, Tzschucke, C. Christoph, Hartwig, John F
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
HALIDES
ROUTE
HETEROARENES
DIALKOXYBORANE
CROSS-COUPLING REACTION
BIS(PINACOLATO)DIBORON
IRIDIUM COMPLEXES
ESTERS
BOND FORMATION
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Summary:The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol062903o