title: Cross-Coupling Synthesis of Methylallyl Alkenes: Scope Extension and Mechanistic Study.
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.
authors.affiliation: 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. clemence.tabele@ap-hm.fr.
authors.forename: Clémence
authors.initials: C
authors.lastname: Tabélé
authors.affiliation: 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. christophe.curti@univ-amu.fr.
authors.forename: Christophe
authors.initials: C
authors.lastname: Curti
authors.affiliation: 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. youssef.kabri@univ-amu.fr.
authors.forename: Youssef
authors.initials: Y
authors.lastname: Kabri
authors.affiliation: 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. nicolas.primas@univ-amu.fr.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Primas
authors.affiliation: 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. patrice.vanelle@univ-amu.fr.
authors.forename: Patrice
authors.initials: P
authors.lastname: Vanelle
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D008738:Methyl Ethers / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry
chemical_list: C000599271:2-methyl-2-propen-1-ol; D000475:Alkenes; D001897:Boronic Acids; D008738:Methyl Ethers; D020005:Propanols; C042581:dimethoxymethane
keywords: allyl alcohol; boronic acids; cross-coupling reactions; palladium