| Autor: |
Droege DG; Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States., Parker AL; Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States., Milligan GM; Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States., Jenkins R; Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States., Johnstone TC; Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States. |
| Abstrakt: |
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. |
