Abstract
Highly selective C(sp2)–C(sp2) cross-coupling of dihalogenated hydrocarbons comprising C(sp2)–Br and C(sp3)–Cl bonds with arylboronic acids is reported. This highly selective coupling reaction of the C(sp2)–Br bond is successfully achieved using Pd(OAc)2 and PCy3·HBF4 as the palladium source and ligand, respectively. A series of chloromethyl-1,1′-biphenyl compounds are obtained in moderate-to-excellent yields. Moreover, this protocol can be extended to the one-pot dual arylation of 1-bromo-4-(chloromethyl)benzene with two arylboronic acids, leading to diverse unsymmetrical 4-benzyl-1,1′-biphenyl derivatives.
Highlights
Transition-metal-catalyzed cross-coupling reactions between electrophiles and arylboronic acids are an important method in the C–C bond formation [1,2,3]
Pd(PPh3 )4 -catalyzed selective coupling reaction of C(sp3 )–Br at the benzylic position of the starting bromobenzyl bromides with arylboronic acids, affording C(sp3 )–C(sp2 ) as the coupling products (Scheme 1a) [11,12]
The results indicated that neither the electronic arylboronic acids were investigated
Summary
Transition-metal-catalyzed cross-coupling reactions between electrophiles and arylboronic acids are an important method in the C–C bond formation [1,2,3]. To the best of our knowledge, the selective reaction of dihalogenated hydrocarbons containing the C(sp2 )–X and C(sp3 )–X bonds with arylboronic acids in the presence of palladium catalyst has been rarely reported [11,12,13,14,15,16]. Pd(PPh3 )4 -catalyzed selective coupling reaction of C(sp3 )–Br at the benzylic position of the starting bromobenzyl bromides with arylboronic acids, affording C(sp3 )–C(sp2 ) as the coupling products (Scheme 1a) [11,12]. In 2010, Maseras conducted an experimental and theoretical study on the role of phosphine ligands in palladium-catalyzed Suzuki cross-coupling of competitive and selective C(sp3 )–Br versus
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