A Facile and Reliable Method for the Synthesis of Tetrabenzoporphyrin from 4,7‐Dihydroisoindole

Abstract

A new route to tetrabenzoporphyrins from the closest possible precursor of the unstable isoindole was developed. A key feature of this route is a dramatic facilitation of the aromatization of annelated rings, which is the most serious bottleneck in previous syntheses of tetrabenzoporphyrins. The capabilities of the new method are illustrated by the syn-

Bright, “Clickable” Porphyrins for the Visualization of Oxygenation under Ambient Light

“…[22,23] Briefly, the intermediate 6 was prepared by a Lindsey-type condensation of the pivaloyl-protected tetrahydroisoindole 5 . Insertion of platinum or palladium yielded the metallated cyclohexenyl porphyrins 7 and 8 .…”

A Versatile General Approach to the Synthesis of Linearly Annelated π-Extended Porphyrins via 4,7-Dihydroisoindole Derivatives

“…The first attempt to prepare 4,7-dihydroisoindole 1 [22] indeed resulted in a failure and explicit statement of its poor stability and overall inapplicability towards the porphyrin chemistry. This instability, however, as we have shown [23] was accounted for not by innate character of the compound, but rather by the way of synthesis used, and the same compound obtained using the Barton-Zard reaction turned out to be as stable as any other known 3,4-dialkylpyrrole.…”

Systematic Investigation of Porphyrin‐Thiophene Conjugates for Ternary Bulk Heterojunction Solar Cells

“…The synthesis of the benzoporphyrin derivatives started from condensation of 4,7‐dihydro‐2 H ‐isoindole and a corresponding aldehyde, followed by oxidation in the presence of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) or tetrachloro‐1,4‐benzoquinone ( p ‐chloranil) as shown in Scheme b. Subsequent aromatization of H‐TPBP with five equivalents of DDQ and then Zn‐metallization of the resulting TPBP afforded Zn‐TPBP in 15% overall yield (from 4,7‐dihydro‐2 H ‐isoindole) . In a similar manner, Zn‐H‐TTBP and Zn‐H‐T2TBP were obtained from the above‐mentioned condensation process, followed by Zn‐metallation.…”