Work

Synthesis and Functionalization of Challenging meso-Substituted Aryl Bis-pocket Porphyrins Accessed via Suzuki–Miyaura Cross-Coupling

Year: 2022

Type: article

Abstract: Herein we report an investigation into the synthesis, metalation, and functionalization of bis-pocket porphyrins using the Suzuki–Miyaura cross-coupling reaction. Steric limitations to accessing bis-pocket porphyrins were overcome by using this Pd-catalyzed C–C-bond-forming strategy to introduce steric bulk after macrocyclization: 2,6-dibromo-4-trimethylsilybenzaldehyde was condensed with pyrrole, and a variety of boronic acids were coupled to the resulting porphyrin in up to 95% yield. Furthermore, we show that these porphyrins can be metalated with a variety of metals and sulfonated to create water-soluble bis-pocket porphyrins.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.2c01538

Authors: Daniel G. Droege, A. Leila Parker, Griffin M. Milligan, Robert Jenkins, Timothy C. Johnstone

Institution: University of California, Santa Cruz

Language: English

Topic: Porphyrin and Phthalocyanine Chemistry

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: University of California, Santa Cruz, Achievement Rewards for College Scientists Foundation, Hellman Foundation, Division of Chemistry