Direct C–H borylation of vinylporphyrins via copper catalysis??

Organic & Biomolecular Chemistry Pub Date: 2022-02-10 DOI: 10.1039/D1OB02005F

Abstract

A method of direct borylation of vinyl-substituted porphyrinoids (porphyrins and chlorins) has been developed based on the copper catalyzed vinylic C–H activation. Ni(II) complexes of meso- and β-vinylporphyrinoids have been transformed to the corresponding pinacolboronated derivatives with good yields and high (E)-stereoselectivity. The method provides an easy and direct access to the valuable synthons which were shown to act as nucleophylic partners in the Suzuki cross-coupling building tetrapyrrole derivatives with π-conjugation through the carbon–carbon double bond.

Graphical abstract: Direct C–H borylation of vinylporphyrins via copper catalysis
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