Selective Approaches to α- and β-Arylated Vinyl Ethers
Anna Domzalska-Pieczykolan1, Ignacio Funes-Ardoiz2, Bartłomiej Furman3
1Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Angewandte Chemie (International Ed. in English)
|November 10, 2021
Summary
We developed simple and efficient palladium-catalyzed methods for regioselective vinyl ether arylation. These reactions are economical, minimize waste, and are applicable to complex molecules like glucal and isochromene.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Vinyl ethers are versatile building blocks in organic synthesis.
- Palladium-catalyzed cross-coupling reactions are crucial for C-C bond formation.
- Regioselective functionalization of vinyl ethers remains a synthetic challenge.
Purpose of the Study:
- To develop simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of vinyl ethers.
- To broaden the substrate scope for vinyl ether arylation, including complex structures.
- To understand the factors governing regioselectivity through computational studies.
Main Methods:
- Palladium-catalyzed α- and β-arylation reactions.
- Utilized structurally diverse vinyl ethers as substrates.
- Employed mild reaction conditions.
- Performed density functional theory (DFT) calculations.
Main Results:
- Achieved simple and efficient protocols for regioselective α- and β-arylations.
- Demonstrated broad substrate scope, including complex arylated glucal and isochromene.
- Reactions proceeded under mild conditions without large reagent excess, enhancing economic viability and reducing waste.
- DFT studies provided insights into regioselectivity-determining factors.
Conclusions:
- Developed practical and economical methods for vinyl ether arylation.
- The protocols are applicable to complex molecules, expanding synthetic possibilities.
- Computational insights aid in understanding and controlling regioselectivity in palladium catalysis.
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