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Syntheses of Benzo[b]furan-6-carbonitrile and 6-Cyanobenzo[b]furan-2-boronic Acid Pinacol Ester.

ABSTRACT: 6-Cyanobenzo[b]furan-2-boronic acid pinacol ester (10) is a potentially useful 2-point scaffold for the construction of specific compounds or compound libraries with benzofuran cores. Using a per-iodination/de-iodination strategy coupled with a Sonogashira alkynylation and Cu-catalyzed heteroannulation, we have developed a procedure that allows the preparation of benzo[b]furan-6-carbonitrile (9) and 6-cyanobenzo[b]furan-2-boronic acid pinacol ester (10) in gram quantities.

SUBMITTER: Williams JD

PROVIDER: S-EPMC3829476 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Syntheses of Benzo[b]furan-6-carbonitrile and 6-Cyanobenzo[b]furan-2-boronic Acid Pinacol Ester.

Williams John D JD Ding Xiaoyuan X Nguyen Son S Vines Kimberly K KK Peet Norton P NP

Synthetic communications 20130101 14

6-Cyanobenzo[b]furan-2-boronic acid pinacol ester (10) is a potentially useful 2-point scaffold for the construction of specific compounds or compound libraries with benzofuran cores. Using a per-iodination/de-iodination strategy coupled with a Sonogashira alkynylation and Cu-catalyzed heteroannulation, we have developed a procedure that allows the preparation of benzo[b]furan-6-carbonitrile (9) and 6-cyanobenzo[b]furan-2-boronic acid pinacol ester (10) ...[more]

PMID: 24249920

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