title: The Suzuki-Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction.
abstract: The efficient Suzuki-Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo, and iodopyrazoles in the Suzuki-Miyaura reaction revealed that Br and Cl derivatives were superior to iodopyrazoles, as a result of reduced propensity to dehalogenation. Moreover, the mechanism and factors affecting the undesired dehalogenation side reaction were revealed.
authors.affiliation: Institute of Molecular and Translation Medicine, Faculty of Medicine, Palacký University , Hněvotínská 5, 77900 Olomouc, Czech Republic.
authors.forename: Lukáš
authors.identifier: 0000-0002-1324-8043
authors.initials: L
authors.lastname: Jedinák
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 17. listopadu 1192/12, 77146 Olomouc, Czech Republic.
authors.forename: Renáta
authors.initials: R
authors.lastname: Zátopková
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 17. listopadu 1192/12, 77146 Olomouc, Czech Republic.
authors.forename: Hana
authors.initials: H
authors.lastname: Zemánková
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 17. listopadu 1192/12, 77146 Olomouc, Czech Republic.
authors.forename: Alena
authors.initials: A
authors.lastname: Šustková
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 17. listopadu 1192/12, 77146 Olomouc, Czech Republic.
authors.forename: Petr
authors.identifier: 0000-0002-7434-6069
authors.initials: P
authors.lastname: Cankař