HFIP as a versatile solvent in resorcin[n]arene synthesis
Hormoz Khosravi1, Valeria Stevens1, Raúl Hernández Sánchez1,2
1Department of Chemistry, Rice University, 6100 Main St., Houston, Texas 77005, USA.
Beilstein Journal of Organic Chemistry
|October 8, 2024
Summary
We discovered 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) efficiently synthesizes resorcin[n]arenes. This method tolerates challenging precursors, yielding diverse products rapidly and in high amounts.
Area of Science:
- Organic Synthesis
- Supramolecular Chemistry
- Green Chemistry
Background:
- Resorcin[n]arene synthesis traditionally requires harsh conditions.
- Certain resorcinol precursors with electron-withdrawing groups or halogens are difficult to cyclize.
- Efficient and mild synthetic routes for diverse resorcin[n]arenes are needed.
Purpose of the Study:
- To develop a novel, efficient, and mild method for synthesizing resorcin[n]arenes.
- To investigate the utility of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent for this transformation.
- To demonstrate the tolerance of challenging resorcinol substrates.
Main Methods:
- Utilizing catalytic amounts of HCl in HFIP solvent.
- Performing the reaction at ambient temperature.
- Employing a one-step cyclization process.
Main Results:
- Successful synthesis of resorcin[n]arenes using HFIP and HCl.
- High yields (up to 98%) achieved for various 2-substituted resorcin[n]arenes.
- Demonstrated tolerance of resorcinols bearing electron-withdrawing groups and halogens, previously considered challenging precursors.
Conclusions:
- HFIP is an effective and efficient solvent for the rapid synthesis of resorcin[n]arenes.
- The developed method offers a mild and versatile approach, accommodating difficult substrates.
- This provides a valuable new synthetic strategy for accessing diverse resorcin[n]arene structures.
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