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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions
1Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Chemical Reviews
|April 17, 2024
Summary
Transition metal catalysis enables direct functionalization of unprotected alcohols in organic synthesis. This review covers deoxygenative functionalizations, etherifications, and chain functionalizations for creating complex molecules.
Area of Science:
- Organic Chemistry
- Catalysis
Background:
- Alcohols are versatile and abundant feedstock molecules.
- Traditional functionalization often requires alcohol activation.
- Recent advances allow direct use of unprotected alcohols.
Purpose of the Study:
- To review transition metal-catalyzed transformations of unprotected alcohols.
- To categorize these reactions into deoxygenative functionalizations, etherifications, and chain functionalizations.
- To highlight the direct harnessing of alcohols in organic synthesis.
Main Methods:
- Focus on transition metal catalysis for alcohol functionalization.
- Classification of reactions based on C-O bond, O-H bond, and C-H bond derivatization.
- Discussion of intermolecular arylation, alkylation, and related reactions.
Main Results:
- Deoxygenative functionalizations enable C-C bond formation by using alcohols as leaving groups.
- Etherifications, modernized classical reactions, offer mild conditions and high selectivity.
- Chain functionalizations utilize the alcohol group to mediate C-H functionalization of the alkyl chain.
Conclusions:
- Transition metal catalysis provides powerful tools for direct alcohol functionalization.
- These methods expand the synthetic utility of alcohols, bypassing the need for pre-activation.
- Catalysis facilitates the construction of complex molecules directly from abundant alcohol feedstocks.
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