Combining the diaza-Diels-Alder reaction and palladium-catalyzed aminations to prepare amino-substituted porphyrins

Goh, Mean See, Pfrunder, Michael, McMurtrie, John, & Arnold, Dennis (2014) Combining the diaza-Diels-Alder reaction and palladium-catalyzed aminations to prepare amino-substituted porphyrins. Asian Journal of Organic Chemistry, 3(8), pp. 856-869.

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A strategy to tackle the synthesis of azoporphyrins with unsubstituted terminal meso positions was investigated. It comprised the combination of diaza-Diels–Alder (DADA) reaction of 1,3-dienes with dialkyl azodicarboxylates, decarboxylative hydrolysis of the bis(carbamates), palladium-catalyzed amination of bromoporphyrin precursors, and retro-DADA reactions to release the ultimate targets. The somewhat confused historical results on the DADA reactions of 1,3-cyclohexadiene were clarified, but the hydrolyses yielded extremely air-sensitive amines which decomposed completely in minutes via autooxidation and retro-DADA reaction. With anthracene or 2,3-dimethyl-1,3-butadiene as the diene, the synthesis of azoporphyrin was not achieved but three amino-substituted porphyrins were obtained in moderate yields under mild conditions. The X-ray crystal structures of several of the intermediates and the final aminoanthracene-porphyrin nickel(II) complex were determined.

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ID Code: 88873
Item Type: Journal Article
Refereed: Yes
DOI: 10.1002/ajoc.201402049
ISSN: 2193-5807
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 08 Oct 2015 04:39
Last Modified: 08 Oct 2015 04:39

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