Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 18, Pages 5925-5929Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900010
Keywords
aromaticity; macrocycles; porphyrinoids; skeletal rearrangement
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Funding
- Shanghai Municipal Science and Technology Major Project [2018SHZDZX03]
- international Cooperation Program of Shanghai Science and Technology Committee [17520750100]
- NSFC [21772041, 21702062, 21811530005]
- Program of Introducing Talents of Discipline to Universities [B160170, JP15K13646, JP16K05700, JP17H05377]
- Japan Society for the Promotion of Science (JSPS)
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A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique pi-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.
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