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Molecules 2015, 20(12), 22890-22899; doi:10.3390/molecules201219886

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

Aix-Marseille Université, CNRS, ICR, UMR 7273, Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin–CS30064, 13385 Marseille cedex 05, France
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Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 November 2015 / Revised: 9 December 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

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. View Full-Text
Keywords: palladium; cross-coupling reactions; boronic acids; allyl alcohol palladium; cross-coupling reactions; boronic acids; allyl alcohol
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tabélé, C.; Curti, C.; Kabri, Y.; Primas, N.; Vanelle, P. Cross-Coupling Synthesis of Methylallyl Alkenes: Scope Extension and Mechanistic Study. Molecules 2015, 20, 22890-22899.

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