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

Molecules

Clémence Tabélé²  Christophe Curti²  Youssef Kabri²  Nicolas Primas²  Patrice Vanelle¹ 

[1] 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

关键词: palladium;    cross-coupling reactions;    boronic acids;    allyl alcohol;   

DOI  :  10.3390/molecules201219886

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.