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Regioselective Oxidative Arylation of Fluorophenols
Congjun Yu1, Frederic W Patureau1
1Institute of Organic Chemistry, RWTH, Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Angewandte Chemie (International Ed. in English)
|October 5, 2019
Summary
This study introduces a metal-free oxidative arylation of fluorophenols. The position of the fluoride determines if the product is a 1,2 or 1,4 arylated quinone, showcasing a versatile new reaction.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Catalysis
Background:
- Oxidative arylation reactions are crucial for constructing complex organic molecules.
- Developing metal-free catalytic systems is a key goal in sustainable chemistry.
- Regioselectivity in arylation reactions, particularly with substituted phenols, remains a challenge.
Purpose of the Study:
- To develop a novel, metal-free, and highly regioselective oxidative arylation of fluorophenols.
- To investigate the influence of the fluoride leaving group's position on the reaction outcome.
- To establish a versatile and general synthetic strategy for arylated quinone derivatives.
Main Methods:
- Employing a metal-free reaction system for the oxidative arylation of fluorophenols.
- Utilizing the inherent electronic and steric properties of ortho- and para-fluorophenols.
- Characterization of the resulting arylated quinone products using spectroscopic techniques.
Main Results:
- Achieved a highly regioselective oxidative, defluorinative arylation of fluorophenols.
- Demonstrated that the position of the fluoride leaving group dictates the regiochemical outcome (1,2- vs. 1,4-arylation).
- Successfully synthesized diverse arylated quinone products, highlighting the reaction's versatility.
Conclusions:
- The described method offers a powerful and sustainable approach to synthesizing arylated quinones.
- The regioselectivity is precisely controlled by the substrate's fluorine substitution pattern.
- This oxidative, defluorinative, arylation concept provides a general and adaptable synthetic tool.
Keywords:
arylated quinonecross dehydrogenative couplingfluorophenolshypervalent iodineregioselective arylationMore Related Videos
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