Efficient access to β - vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

Vinicius R Campos; Ana T P C Gomes; Anna C Cunha; Maria da Graça P M S Neves; Vitor F Ferreira; José A S Cavaleiro

doi:10.3762/bjoc.13.22

Efficient access to β - vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

Beilstein J Org Chem. 2017 Jan 30:13:195-202. doi: 10.3762/bjoc.13.22. eCollection 2017.

Authors

Vinicius R Campos¹, Ana T P C Gomes², Anna C Cunha³, Maria da Graça P M S Neves², Vitor F Ferreira³, José A S Cavaleiro²

Affiliations

¹ Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil; QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
² QOPNA and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
³ Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, 24020-150 Niterói, RJ, Brazil.

Abstract

This work describes a new approach to obtain new β-vinylporphyrin derivatives through palladium-catalyzed cross-coupling reaction of 2-bromo-5,10,15,20-tetraphenylporphyrinatozinc(II) with N-tosylhydrazones. This is the first report of the use of such synthetic methodology in porphyrin chemistry allowing the synthesis of new derivatives, containing β-arylvinyl substituents.

Keywords: N-tosylhydrazones; Pd-catalyzed cross coupling; porphyrins.