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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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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. |
format | Online Article Text |
id | pubmed-3678591 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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