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Direct Assembly of Prenylated Heteroarenes through a Cascade Minisci Reaction/Dehydration Sequence.

ABSTRACT: The prenyl group is an important component in bioactive compounds. Herein, we report the assembly of prenylated heteroarenes through a cascade Minisci reaction and acid-promoted dehydration sequence. The use of potassium (3-hydroxy-3-methylbut-1-yl)trifluoroborate as a new coupling reagent allows the direct introduction of prenyl and 3-hydroxy-3-methylbutyl groups to a wide variety of electron-deficient heteroarenes. Synthetic application is also demonstrated.

SUBMITTER: Tan DH

PROVIDER: S-EPMC5167326 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Direct Assembly of Prenylated Heteroarenes through a Cascade Minisci Reaction/Dehydration Sequence.

Tan Dong-Hang DH Zeng Yao-Fu YF Liu Yao Y Lv Wen-Xin WX Li Qingjiang Q Wang Honggen H

ChemistryOpen 20161011 6

The prenyl group is an important component in bioactive compounds. Herein, we report the assembly of prenylated heteroarenes through a cascade Minisci reaction and acid-promoted dehydration sequence. The use of potassium (3-hydroxy-3-methylbut-1-yl)trifluoroborate as a new coupling reagent allows the direct introduction of prenyl and 3-hydroxy-3-methylbutyl groups to a wide variety of electron-deficient heteroarenes. Synthetic application is also demonstrated. ...[more]

PMID: 28032022

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