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

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 th...

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Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2016-12, Vol.5 (6), p.535-539
Main Authors: Tan, Dong‐Hang, Zeng, Yao‐Fu, Liu, Yao, Lv, Wen‐Xin, Li, Qingjiang, Wang, Honggen
Format: Article
Language:English
Subjects:
Assembly
Biocompatibility
Cascade chemical reactions
Cascades
Communication
Communications
Coupling
Dehydration
heteroarenes
Minisci reaction
Potassium
prenylation
radical addition
Reagents
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Summary: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. Prenylated heteroarenes: The prenyl group is prevalent as an important component in bioactive compounds. The assembly of prenylated heteroarenes is realized 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 direct introduction of prenyl and 3‐hydroxy‐3‐methylbutyl groups to a wide variety of electron‐deficient heteroarenes.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.201600096