Cross-Coupling Synthesis of Methylallyl Alkenes: Scope Extension and Mechanistic Study

Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2015-12, Vol.20 (12), p.22890-22899
Main Authors: Tabélé, Clémence, Curti, Christophe, Kabri, Youssef, Primas, Nicolas, Vanelle, Patrice
Format: Article
Language:English
Subjects:
Acidity
Acids
Alkenes
Alkenes - chemistry
allyl alcohol
boronic acids
Boronic Acids - chemistry
Catalysis
Chemical reactions
Chemical Sciences
Cross coupling
cross-coupling reactions
Isomerization
Methyl Ethers - chemistry
Organic chemistry
palladium
Propanols - chemistry
Side reactions
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Summary:Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields under mild reaction conditions that decrease these side reactions. The scope of this environmentally benign reaction is thereby extended to a wide variety of boronic acids. A mechanistic study was conducted and suggested a plausible catalytic cycle mechanism, pointing to the importance of the Lewis acidity of the boronic acid used.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules201219886