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Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C–H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)(2), the ortho-C–H bond of benzylpicolinamides is first ary...

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Detalles Bibliográficos
Autores principales: Pearson, Ryan, Zhang, Shuyu, He, Gang, Edwards, Nicola, Chen, Gong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678591/
https://www.ncbi.nlm.nih.gov/pubmed/23766804
http://dx.doi.org/10.3762/bjoc.9.102
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author Pearson, Ryan
Zhang, Shuyu
He, Gang
Edwards, Nicola
Chen, Gong
author_facet Pearson, Ryan
Zhang, Shuyu
He, Gang
Edwards, Nicola
Chen, Gong
author_sort Pearson, Ryan
collection PubMed
description We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C–H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)(2), the ortho-C–H bond of benzylpicolinamides is first arylated with an aryl iodide. The resulting biaryl compound is then subjected to palladium-catalyzed picolinamide-directed intramolecular dehydrogenative C–H amination with PhI(OAc)(2) oxidant to form the corresponding cyclized dihydrophenanthridines. The benzylic position of these dihydrophenanthridines could be further oxidized with Cu(OAc)(2), removing the picolinamide group and providing phenathridine products. The cyclization and oxidation could be carried out in a single step and afford phenathridines in moderate to good yields.
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spelling pubmed-36785912013-06-13 Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization Pearson, Ryan Zhang, Shuyu He, Gang Edwards, Nicola Chen, Gong Beilstein J Org Chem Letter We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C–H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)(2), the ortho-C–H bond of benzylpicolinamides is first arylated with an aryl iodide. The resulting biaryl compound is then subjected to palladium-catalyzed picolinamide-directed intramolecular dehydrogenative C–H amination with PhI(OAc)(2) oxidant to form the corresponding cyclized dihydrophenanthridines. The benzylic position of these dihydrophenanthridines could be further oxidized with Cu(OAc)(2), removing the picolinamide group and providing phenathridine products. The cyclization and oxidation could be carried out in a single step and afford phenathridines in moderate to good yields. Beilstein-Institut 2013-05-08 /pmc/articles/PMC3678591/ /pubmed/23766804 http://dx.doi.org/10.3762/bjoc.9.102 Text en Copyright © 2013, Pearson et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Pearson, Ryan
Zhang, Shuyu
He, Gang
Edwards, Nicola
Chen, Gong
Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title_full Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title_fullStr Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title_full_unstemmed Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title_short Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization
title_sort synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential c–h functionalization
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678591/
https://www.ncbi.nlm.nih.gov/pubmed/23766804
http://dx.doi.org/10.3762/bjoc.9.102
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