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Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing
Jignesh J Patel1, Marju Laars1, Wei Gan1
1Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, ON, K7L 3N6, Canada.
Angewandte Chemie (International Ed. in English)
|May 31, 2018
Summary
Researchers developed a novel carbanionic reaction sequence for synthesizing highly substituted 2-naphthols from coumarins. This method utilizes directed remote metalation for efficient ring closure, yielding aryl 2-naphthols in high amounts.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Carbanion Chemistry
Background:
- 2-naphthols are important structural motifs in various organic compounds.
- Existing synthetic routes for highly substituted 2-naphthols can be complex and low-yielding.
Purpose of the Study:
- To develop a general and efficient synthesis of highly substituted 2-naphthols.
- To explore a novel carbanionic reaction sequence utilizing directed remote metalation.
Main Methods:
- Ring opening of coumarins using lithium bases (LiNEt2 or LiNiPr2) to form Z-cinnamamides.
- In situ generation of a directing group and subsequent lateral directed remote metalation.
- Ring closure to afford aryl 2-naphthols.
Main Results:
- Successful synthesis of highly substituted 2-naphthols in good to excellent yields.
- Demonstration of a one-pot process combining multiple transformations.
- Elucidation of the mechanism, highlighting the necessity of the Z-cinnamamide intermediate.
Conclusions:
- The developed carbanionic reaction sequence provides a versatile route to highly substituted 2-naphthols.
- The methodology is applicable to the synthesis of complex molecules like 3,3'-diaryl BINOL ligands.
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