Exploiting the Bis-Nucleophilicity of α‑Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides

α-Aminoboronate salts are interesting examples of heteroatomic species containing adjacent nucleophilic centers. We have developed an acylation/arylation reaction using 2-bromobenzoyl chlorides as bis-electrophiles that harnesses the nucleophilicity of both positions, leading to isoindolinones. The...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 8; pp. 1848 - 1851
Main Authors Dumas, Aaron M, Sieradzki, Adrian J, Donnelly, Liam J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.04.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISOINDOLINONES
BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE
ACID-DERIVATIVES
CROSS-COUPLING REACTIONS
ASYMMETRIC-SYNTHESIS
PINACOLBORYL ADDITION
ALPHA-(ACYLAMINO)BENZYLBORONIC ESTERS
BORONIC ESTERS
ARYL
C-H BONDS
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Summary:α-Aminoboronate salts are interesting examples of heteroatomic species containing adjacent nucleophilic centers. We have developed an acylation/arylation reaction using 2-bromobenzoyl chlorides as bis-electrophiles that harnesses the nucleophilicity of both positions, leading to isoindolinones. The reactions proceed under mild conditions via an intramolecular, Cu-catalyzed sp3–sp2 coupling, giving products in up to 95% yield. These conditions enable arylation of α,α-disubstituted aminoboronates, which are difficult to accomplish using methods based on less abundant and more expensive transition metals.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00586