Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling
Tetrahedron(2008)
Abstract
Microwave irradiation efficiently promoted the solid-phase Suzuki–Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue.
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Key words
Histidine,Arylation,Suzuki–Miyaura cross-coupling,Microwave,Biaryl peptides,Solid-phase synthesis
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