Palladium-Catalyzed Annulation of Internal Alkynes: Direct Access to π‑Conjugated Ullazines
A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers...
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| Published in | Organic letters Vol. 18; no. 12; pp. 2876 - 2879 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
17.06.2016
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.6b01182 |
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| Abstract | A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C–H functionalization in the construction of organic optoelectronic materials. |
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| AbstractList | A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C–H functionalization in the construction of organic optoelectronic materials. A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C–H functionalization in the construction of organic optoelectronic materials. A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C-H functionalization in the construction of organic optoelectronic materials.A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C-H functionalization in the construction of organic optoelectronic materials. A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various p-conjugated indolizino[6,5,4,3-ija]quinolones (ullazines) with a reactive functional group tolerance. As illustrative examples, three new ullazine-based sensitizers are synthesized, and the performance of these dyes is examined in DSSC devices, which demonstrates the potential of direct C-H functionalization in the construction of organic optoelectronic materials. |
| Author | You, Jingsong Li, Xiaoyu Wan, Danyang Wang, Ruilin Jiang, Ruyong Feng, Boya Lan, Jingbo |
| AuthorAffiliation | Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School Sichuan University College of Materials Science and Engineering |
| AuthorAffiliation_xml | – name: Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Medical School – name: College of Materials Science and Engineering – name: Sichuan University |
| Author_xml | – sequence: 1 givenname: Danyang surname: Wan fullname: Wan, Danyang – sequence: 2 givenname: Xiaoyu surname: Li fullname: Li, Xiaoyu – sequence: 3 givenname: Ruyong surname: Jiang fullname: Jiang, Ruyong – sequence: 4 givenname: Boya surname: Feng fullname: Feng, Boya – sequence: 5 givenname: Jingbo surname: Lan fullname: Lan, Jingbo – sequence: 6 givenname: Ruilin surname: Wang fullname: Wang, Ruilin – sequence: 7 givenname: Jingsong surname: You fullname: You, Jingsong email: jsyou@scu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27227659$$D View this record in MEDLINE/PubMed |
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| Keywords | HETEROARENES DESIGN SOLAR-CELLS HYDROCARBONS ARYLATION BONDS OXIDATIVE ANNULATION C-H ACTIVATION MOLECULES |
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| Snippet | A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various π-conjugated... A palladium-catalyzed cyclization reaction of 1-(2,6-dibromophenyl)-1H-pyrroles with alkynes has been developed to construct various p-conjugated... |
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| SubjectTerms | alkynes carbon-hydrogen bond activation catalytic activity Chemistry Chemistry, Organic cyclization reactions dyes electronic equipment moieties palladium Physical Sciences quinolones Science & Technology |
| Title | Palladium-Catalyzed Annulation of Internal Alkynes: Direct Access to π‑Conjugated Ullazines |
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