biostudies-literatureDroege DGDivision of ChemistryUniversity of California, Santa CruzHellman FoundationAchievement Rewards for College Scientists Foundation11783-11795https://www.ebi.ac.uk/biostudies/studies/S-EPMC9447288biostudies-literatureUnknown87(17)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 <i>after</i> 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.The Journal of organic chemistrySynthesis and Functionalization of Challenging <i>meso</i>-Substituted Aryl Bis-pocket Porphyrins Accessed via Suzuki-Miyaura Cross-Coupling.PMC94472882018501Parker ALJohnstone TCJenkins RDroege DGMilligan GMfalseSynthesis and Functionalization of Challenging <i>meso</i>-Substituted Aryl Bis-pocket Porphyrins Accessed via Suzuki-Miyaura Cross-Coupling.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 <i>after</i> 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.2022-01-01T00:00:00Z2022 Sep2024-11-07T03:41:35.246Z2024-11-07T03:41:35.246ZS-EPMC94472883597679110.1021/acs.joc.2c01538