Brønsted Acid‐Catalysed Dehydrative Substitution Reactions of Alcohols
Open Access
- 3 June 2020
- journal article
- review article
- Published by Wiley in Chemistry – A European Journal
- Vol. 27 (1), 106-120
- https://doi.org/10.1002/chem.202002106
Abstract
The direct, catalytic dehydrative substitution of alcohols is a challenging, yet highly desirable process in the development of more sustainable approaches to organic chemistry. This review outlines recent advances in Brønsted acid‐catalysed dehydrative substitution reactions for C‐C, C‐O, C‐N and C‐S bond formation. The wide range of processes that are now accessible using simple alcohols as the formal electrophile are highlighted, while current limitations and therefore possible future directions for research are also discussed. The direct, catalytic dehydrative substitution of alcohols is a challenging, yet highly desirable process in the development of more sustainable approaches to organic chemistry. This review outlines recent advances in Brønsted acid‐catalysed dehydrative substitution reactions for C‐C, C‐O, C‐N and C‐S bond formation. The wide range of processes that are now accessible using simple alcohols as the formal electrophile are highlighted, while current limitations and therefore possible future directions for research are also discussed.Funding Information
- Engineering and Physical Sciences Research Council (Doctoral Training Account (University of St Andrews))
This publication has 99 references indexed in Scilit:
- Brønsted-Säure-katalysierte konjugierte Addition von β-Dicarbonylverbindungen an in situ erzeugteortho-Chinomethide - enantioselektive Synthese von 4-Aryl-4H-chromenenAngewandte Chemie, 2014
- The development of catalytic nucleophilic substitution reactions: challenges, progress and future directionsOrganic & Biomolecular Chemistry, 2014
- Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo‐ and Heterocyclizations of Free Allylic AlcoholsAngewandte Chemie, 2012
- Boronic Acid Catalysis as a Mild and Versatile Strategy for Direct Carbo- and Heterocyclizations of Free Allylic AlcoholsAngewandte Chemie, 2012
- Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric SynthesisThe Journal of Organic Chemistry, 2011
- Enantioselective Brønsted Acid Catalysis in the Friedel-Crafts Reaction of Indoles with Secondary ortho-Hydroxybenzylic AlcoholsSynlett, 2011
- Chiral Organic Contact Ion Pairs in Metal-Free Catalytic Asymmetric Allylic SubstitutionsJournal of the American Chemical Society, 2011
- Organocatalyzed Friedel–Crafts arylation of benzylic alcoholsTetrahedron Letters, 2010
- Boronic Acid Catalyzed Friedel−Crafts Reactions of Allylic Alcohols with Electron-Rich Arenes and Heteroarenes.The Journal of Organic Chemistry, 2010
- Borrowing Hydrogen in the Activation of AlcoholsAdvanced Synthesis & Catalysis, 2007